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

HRID 248189노트

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HRID 248189 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f60824d0d7ad4036b85f4d51636dac67
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208345

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