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

HRID 248189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248189
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f60824d0d7ad4036b85f4d51636dac67
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208345

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