Sodium Chloride → ethyl (2Z)-3-{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}acrylate

HRID 2264630ノート

反応式

HRID 2264630 の反応式
C1(C)C=CC=CC=1OP([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(OC1C=CC=CC=1C)=O.[OH-].[CH2:26]([N+](C)(C)C)C1C=CC=CC=1.CO.[Br:39][C:40]1[CH:45]=[CH:44][C:43]([S:46]([N:49]2[C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:51]=[C:50]2C=O)(=[O:48])=[O:47])=[CH:42][CH:41]=1.[Cl-].[Na+]>C1COCC1>[Br:39][C:40]1[CH:45]=[CH:44][C:43]([S:46]([N:49]2[C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:51]=[C:50]2/[CH:26]=[CH:18]\[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:48])=[O:47])=[CH:42][CH:41]=1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 10593815Ethyl Di-o-tolylphosphonoacetateHCID 19865511Benzyltrimethylammonium hydroxide methanolHCID 442108071-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde

生成物 1

HCID 67044639ethyl (2Z)-3-{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}acrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

To a solution of 0.4 mL of ethyl di-o-tolylphosphonoacetate in 15 mL of THF was added 0.67 g of a 40% benzyltrimethylammonium hydroxide-methanol solution under cooling in a dry ice-acetone bath, and the resulting mixture was stirred at −70° C. for 15 minutes. To the solution, a solution of 0.47 g of 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carbaldehyde in 5 mL of THF was added, the resulting mixture was stirred at −70° C. for 1.5 hours and under cooling in an ice-methanol bath for 1 hour. To the solution, 50 mL of saturated aqueous sodium chloride solution was added, the mixture was extracted with 100 mL of ethyl acetate, the extract was washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:5) to obtain 0.53 g of ethyl (2Z)-3-{1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}acrylate as a pale yellow syrup. ESI−: 432, 434

後処理

  1. temperatureunder cooling in a dry ice-acetone bath
  2. stirringthe resulting mixture was stirred at −70° C. for 1.5 hours
  3. temperatureunder cooling in an ice-methanol bath for 1 hour
  4. extractionthe mixture was extracted with 100 mL of ethyl acetate
  5. washthe extract was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:5)

出典と根拠

ORDレコード
ord-97cd595b10774946a0ddfbc9411f72dc
出典データセット
uspto-grants-2010_12
特許番号
US07855225B2

反応ノート

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