Oxalyl chloride → (2S)-2-((1,1-Dimethylethyl)dimethylsilyloxy)propanoyl chloride

HRID 248189ノート

反応式

HRID 248189 の反応式
[CH3:1][C:2]([Si:5]([CH3:20])([CH3:19])[O:6][C@@H:7]([CH3:18])[C:8](O[Si](C(C)(C)C)(C)C)=[O:9])([CH3:4])[CH3:3].C(Cl)(=O)C([Cl:24])=O>CN(C)C=O.C(Cl)Cl>[CH3:1][C:2]([Si:5]([CH3:20])([CH3:19])[O:6][C@@H:7]([CH3:18])[C:8]([Cl:24])=[O:9])([CH3:4])[CH3:3]

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 16756134(1,1-Dimethylethyl)dimethylsilyl (2S)-2-((1,1-dimethylethyl)dimethylsilyloxy)propanoate

生成物 1

HCID 11031472(2S)-2-((1,1-Dimethylethyl)dimethylsilyloxy)propanoyl chloride収率 88%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 41.0 g (0.13 mol) of 2-(1,1-dimethylethyl)dimethylsilyl (2S)-2-((1,1-dimethylethyl)dimethylsilyloxy)propanoate (7) and five drops of N,N-dimethylformamide in methylene chloride at 0° C. was added 70.8 mL (0.14 mol) of a 2.0M solution of oxalyl chloride in methylene chloride over a 30 minute period. The cooling bath was removed and the reaction mixture was allowed to stir at room temperature for 18 hours. The solvent and excess oxalyl chloride were removed by rotary evaporation resulting in a yellow liquid. Purification by vacuum distillation afforded 25.6 g (88%) of (2S)-2-((1,1 -dimethylethyl)dimethylsilyloxy)propanoyl chloride (8) as a clear liquid: bp 42°-45° C. (1.5 mm Hg); 1H NMR (CDCl3) δ0.0920 (s, 3 H), 0.118 (s, 3 H), 0.909 (s, 9 H), 1.50 (d, J=6.7 Hz, 3 H), 4.49 (q, J=6.7 Hz, 1 H); 13C NMR (CDCl3) δ176.6, 76.0, 25.7, 25.6, 25.3, 20.9, 18.1, -1.57, -5.04, -5.28.

後処理

  1. customThe cooling bath was removed
  2. customThe solvent and excess oxalyl chloride were removed by rotary evaporation
  3. customresulting in a yellow liquid
  4. customPurification
  5. distillationby vacuum distillation

出典と根拠

ORDレコード
ord-f60824d0d7ad4036b85f4d51636dac67
出典データセット
uspto-grants-1993_05
特許番号
US05208345

反応ノート

読み込み中…