Sodium hydride → 2-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl Ester

HRID 2266499ノート

反応式

HRID 2266499 の反応式
[C:1]([S:5][C:6](=[O:11])[CH2:7][C:8](=[O:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1>COCCOC.[Cl-].[NH4+]>[C:1]([S:5][C:6](=[O:11])[CH:7]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1)[C:8](=[O:10])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 140007Butanethioic acid, 3-oxo-, S-(1,1-dimethylethyl) esterHCID 27335814-(Methylsulfonyl)benzyl Bromide

生成物 1

HCID 866314382-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl Ester

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒3 回HCID 25517Ammonium Chloride溶媒

反応条件

温度
0 °C

実験手順

A solution of 3-oxothiobutyric acid S-tert-butyl ester (7.5 g) in 1,2-dimethoxyethane (10 mL) was added to a stirred suspension of sodium hydride (60% in oil, 1.9 g) in 1,2-dimethoxyethane (100 mL) at −20° C. The mixture was warmed to 0° C. for 10 minutes and then a solution of 1-bromomethyl-4-methanesulfonylbenzene (12.9 g) in 1,2-dimethoxyethane (30 mL) was added dropwise over a period of 10 minutes. The resulting mixture was warmed to room temperature over 30 minutes and then stirred at this temperature for 17 hours. The mixture was diluted with saturated aqueous ammonium chloride solution (70 mL) and the phases separated. The aqueous phase was extracted with diethyl ether and the combined organic phases were dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume) gave title compound, 7.1 g.

後処理

  1. temperatureThe resulting mixture was warmed to room temperature over 30 minutes
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted with diethyl ether
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume)

出典と根拠

ORDレコード
ord-559e7a9e997f4b87a5994f3c9ada7549
出典データセット
uspto-grants-2010_12
特許番号
US07858640B2

反応ノート

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