Acetone → 3-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester

HRID 1940196ノート

反応式

HRID 1940196 の反応式
[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[CH:6][C:7](=[O:29])[N:8]([C:14]1[S:15][C:16]([Cl:28])=[CH:17][C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:2].[Cl-].[Cl-].[Cl-].[Cs+].[Cs+].[Cs+].[BH4-].[Na+].CC(C)=O>CO>[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[CH:6][C:7](=[O:29])[N:8]([C:14]1[S:15][C:16]([Cl:28])=[CH:17][C:18]=1[CH:19]([OH:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:2]

参加物

6

反応物 4

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 20975861Cesium trichlorideHCID 702774443-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester

生成物 1

HCID 702775533-[N-[5-Chloro-3-(alpha-hydroxy-2-chlorobenzyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester収率 103.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 3-[N-[5-chloro-3-(2-chlorobenzoyl)-2-thienyl]-N-neopentylcarbamoyl]acrylic acid ethyl ester (2.37 g) and cesium trichloride.heptahydrate (2.98 g) in methanol (100 ml) was gradually added, sodium borohydride (303 mg) at room temperature. The mixture stirred for 20 minutes at room temperature, to which was added acetone, then the solvent was distilled off. To the residue were added 1M potassium hydrogensulfate and acetic acid ethyl ester. The organic layer was washed with a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of a silica-gel column chromatography to give a non-crystalline solid (2.47 g).

後処理

  1. customat room temperature
  2. distillationthe solvent was distilled off
  3. additionTo the residue were added 1M potassium hydrogensulfate and acetic acid ethyl ester
  4. washThe organic layer was washed with a saturated aqueous saline solution
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica-gel column chromatography

出典と根拠

ORDレコード
ord-90c17bfe0b3a43ccac691f5f5ec84f75
出典データセット
uspto-grants-1997_12
特許番号
US05698691

反応ノート

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