Reaxys Anonymous 20121108 002529 577

O N H H
N H O
O O
H O O O racemate
O O
1
O
O
N H N H H H O OH O O racemate
O O Cl O
2.1
2.2
Cl
O
2.3
Cl
O O OH O
O O OH O
O O O OH O
Cl
PCl Cl Cl
Cl
PCl Cl Cl
3.1
3.2
3.3
O
O
3.4
OH O
3.5
O O OH O
O O O O
O
OH
O S O
O O O
HO OH
F F S F O
O O O
4
HO
O F F S
O O O F S F
O F F
O O O
Copyright 2012 Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys is a trademark owned and protected by Elsevier Properties SA and used under license.
1/11
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O
O O
N H N H H H OH
O N H H
N H O
O O
O Cl O
H O O O racemate
O O
O O O racemate
Rx-ID: 10157172 View in Reaxys Yield Conditions & References
95 %
With pyridine, Time= 96h, T= 20 C Stork, Gilbert; Tang, Peng Cho; Casey, Michael; Goodman, Burton; Toyota, Masahiro; Journal of the American Chemical Society; vol. 127; nb. 46; (2005); p. 16255 - 16262 View in Reaxys
2/11
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O O
O O O Cl O
2.1
O OH O
100 %
With thionyl chloride in dichloromethane, Heating Jin, Yi; Zhou, Zu-Yu; Tian, Wei; Yu, Qiang; Long, Ya-Qiu; Bioorganic & Medicinal Chemistry Letters; vol. 16; nb. 22; (2006); p. 5864 - 5869 View in Reaxys
100 %
Example Title 4.1.4. 3,4,5-Trimethoxybenzoyl chloride (20) To a mixture of 3,4,5-trimethoxybenzoic acid (8.00 g, 37.7 mmol) in CHCl3 (30 mL) was added thionyl chloride (13.7 mL, 189 mmol) in a dropwise fashion. Once the addition was completed, the reaction mixture was heated to reflux for 4 h before being cooled back to room temperature. The solvent and excess thionyl chloride was removed under reduced pressure to yield the acyl chloride 20 in quantitative yield as a colourless oil, which was subsequently used without further purification: max/cm-1 (NaCl) 2970, 2944, 1750, 1590, 1457, 1415, 1130, 1128. With thionyl chloride in chloroform, Time= 4h, Reflux Pierce, Larry T.; Cahill, Michael M.; McCarthy, Florence O.; Tetrahedron; vol. 67; nb. 25; (2011); p. 4601 - 4611 View in Reaxys
100 %
Example Title 3,4,5-Trimethoxybenzoyl chloride (74) (Scheme 10). A mixture of acid 29 (3.0 g, 14.1 mmol) and thionyl chloride (4.1 mL, 56.5 mmol) in dichloromethane (25 mL) was refluxed for 3 h. The pale yellow solution was concentrated in vacuo to give the crude acid chloride 7453 (3.26 g, quant.) as a yellow pale solid. 1H NMR (CDCl3, 400 MHz) (ppm) 3.93 (s, 6H, 2OCH3), 3.96 (s, 3H, OCH3), 7.27 (s, 2H, ArH). With thionyl chloride in CH2C3, Time= 3h, Reflux Ghinet, Alina; Rigo, Benoit; Henichart, Jean-Pierre; Le Broc-Ryckewaert, Delphine; Pommery, Jean; Pommery, Nicole; Gautret, Philippe; Thuru, Xavier; Quesnel, Bruno; Bioorganic and Medicinal Chemistry; vol. 19; nb. 20; (2011); p. 6042 - 6054 View in Reaxys
3/11
2012-11-08 00:25:46
O
Cl
O O OH O
O O
O Cl
2.2
Cl
PCl Cl Cl
Perkin; Weizmann; Journal of the Chemical Society; vol. 89; (1906); p. 1655 View in Reaxys
4/11
2012-11-08 00:25:46
O
Cl
O O OH O
O O
O Cl
2.3
Cl
PCl Cl Cl
Graebe; Suter; Justus Liebigs Annalen der Chemie; vol. 340; (1905); p. 230 View in Reaxys
5/11
2012-11-08 00:25:46
O O O OH OH O
3.1
O O
99 %
With dihydrogen peroxide in water, toluene, Time= 4h, T= 20 - 85 C Hu, Yu Lin; Ge, Qiang; Lu, Ming; Ma, Xiao Yun; Acta Chimica Slovenica; vol. 57; nb. 4; (2010); p. 927 - 930 View in Reaxys
93 %
With Cu(II)-complex of salen-H4, dihydrogen peroxide in acetonitrile, Time= 2h, T= 80 C Velusamy, Subbarayan; Punniyamurthy, Tharmalingam; European Journal of Organic Chemistry; nb. 20; (2003); p. 3913 - 3915 View in Reaxys
80 %
With dihydrogen peroxide, oxygen, (2-OPhCH2NHCH2)2(2-)*Co(2+) in acetonitrile, Time= 4h, T= 80 C Das, Subhabrata; Punniyamurthy, T.; Tetrahedron Letters; vol. 44; nb. 32; (2003); p. 6033 - 6036 View in Reaxys
6/11
2012-11-08 00:25:46
O O
O O O
O
3.2
O O
OH O
95 %
Stage 1: With potassium hydroxide in ethanol, water, Time= 3h, Reflux Stage 2: With sulfuric acid in water Takahashi, Rintaro; Nunokawa, Tatsuya; Shibuya, Tadahiro; Tomita, Ryohei; Tatewaki, Yoko; Okada, Shuji; Kimura, Tatsumi; Shimada, Satoru; Matsuda, Hiro; Bulletin of the Chemical Society of Japan; vol. 85; nb. 2; (2012); p. 236 - 244 View in Reaxys Koerner; Gazzetta Chimica Italiana; vol. 18; (1888); p. 215 View in Reaxys With potassium carbonate Herzig; Pollak; Monatshefte fuer Chemie; vol. 25; (1904); p. 513 View in Reaxys Will; Chemische Berichte; vol. 21; (1888); p. 2022 View in Reaxys
7/11
2012-11-08 00:25:46
O O O
3.3
O O O
OH O
90 %
With sodium chlorite in acetonitrile, 1.) 10 deg C, 2 h, 2.) RT, 3 h Babu, B. Ramesh; Balasubramaniam, K. K.; Organic Preparations and Procedures International; vol. 26; nb. 1; (1994); p. 123 - 125 View in Reaxys
85 %
With tetraethylammonium bromide in N,N-dimethyl-formamide, T= 20 C, Oxidation Singh, Sundaram; Singh, Krishna Nand; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 36; nb. 9; (1997); p. 805 - 807 View in Reaxys
84 %
With sodium chlorite in dichloromethane, acetic acid Bayle, J. P.; Perez, F.; Courtieu, J.; Bulletin de la Societe Chimique de France; nb. 4; (1990); p. 565 - 567 View in Reaxys
8/11
2012-11-08 00:25:46
OH O
O
O O S O O
O O OH O
3.4
HO OH
OH
85 % 80 %
Insole, Joan M.; Journal of Chemical Research, Miniprint; nb. 12; (1990); p. 2831 - 2867 View in Reaxys With N-hexadecyl-N,N,N-trimethylammonium bromide in sodium hydroxide, chloroform, Ambient temperature Nath, Swadhin; Bhattacharyya, Anjan; Sengupta, P. K.; Journal of the Indian Chemical Society; vol. 60; (1983); p. 801 - 802 View in Reaxys
76 %
With potassium hydroxide, Time= 3h, Heating Negi, Arvind Singh; Darokar, Mahinder P.; Chattopadhyay, Sunil K.; Garg, Ankur; Bhattacharya, Asish K.; Srivastava, Vandana; Khanuja, Suman P. S.; Bioorganic & Medicinal Chemistry Letters; vol. 15; nb. 4; (2005); p. 1243 - 1248 View in Reaxys
9/11
2012-11-08 00:25:46
O O
O
3.5
F F S F O
O O O
O OH O
94 %
With potassium acetate, 1,1'-bis-(diphenylphosphino)ferrocene, palladium diacetate in dimethyl sulfoxide, Time= 3h, T= 60 C Cacchi, Sandro; Lupi, Alessandro; Tetrahedron Letters; vol. 33; nb. 27; (1992); p. 3939 - 3942 View in Reaxys
10/11
2012-11-08 00:25:46
O O S O F S F
HO
O F F
F F
O O O
F F S F O
O O O
97 %
With potassium phosphate in toluene, T= 0 - 20 C Sajiki, Hironao; Mori, Akinori; Mizusaki, Tomoteru; Ikawa, Takashi; Maegawa, Tomohiro; Hirota, Kosaku; Organic Letters; vol. 8; nb. 5; (2006); p. 987 - 990 View in Reaxys
97 %
With potassium phosphate in water, toluene, T= 0 - 20 C Mori, Akinori; Mizusaki, Tomoteru; Ikawa, Takashi; Maegawa, Tomohiro; Monguchi, Yasunari; Sajiki, Hironao; Tetrahedron; vol. 63; nb. 5; (2007); p. 1270 - 1280 View in Reaxys With potassium phosphate in toluene, T= 0 - 20 C Macmillan, Derek; Anderson, David W.; Organic Letters; vol. 6; nb. 25; (2004); p. 4659 - 4662 View in Reaxys
11/11
2012-11-08 00:25:46

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Rx-ID: 10157172 View in Reaxys Yield Conditions & References

Rx-ID: 820763 View in Reaxys Yield Conditions & References

Rx-ID: 5819483 View in Reaxys Yield Conditions & References

Rx-ID: 5819485 View in Reaxys Yield Conditions & References

Rx-ID: 9458186 View in Reaxys Yield Conditions & References

Rx-ID: 337749 View in Reaxys Yield Conditions & References

Rx-ID: 2432625 View in Reaxys Yield Conditions & References

Rx-ID: 754169 View in Reaxys Yield Conditions & References

Rx-ID: 2003027 View in Reaxys Yield Conditions & References

Rx-ID: 9874262 View in Reaxys Yield Conditions & References

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