Ethyl Acetate → (S)-3-(3-Bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid

HRID 1432107ノート

反応式

HRID 1432107 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9]Br)[CH:3]=1.C([S:14][CH2:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18])(=O)C.[OH-].[Na+].CCOC(C)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH2:9][S:14][CH2:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2724506D-beta-acetylthioisobutyric acidHCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene

生成物 1

HCID 68541731(S)-3-(3-Bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 5.55 g (21 mmol) 1-bromo-3-bromomethyl-5-methyl-benzene and 2.90 ml (21 mmol) (S)-3-acetylsulfanyl-2-methyl-propionic acid in 32 ml methanol is cooled in an ice bath and 4N aqueous sodium hydroxide (15.8 ml, 63 mmol) are added. The reaction mixture is stirred at rt for 3 hrs. EtOAc is added to the mixture and the organic layer is washed with water and brine and evaporated. Filtration over silica gel (flashmaster, hexane to hexane/EtOAc 4/6) gives the title compound.

後処理

  1. washthe organic layer is washed with water and brine
  2. customevaporated
  3. filtrationFiltration over silica gel (flashmaster, hexane to hexane/EtOAc 4/6)

出典と根拠

ORDレコード
ord-25d74e1d243940ddb7790c5ebb43d38c
出典データセット
uspto-grants-2009_11
特許番号
US07612055B2

反応ノート

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