Imidazole → methyl (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropionate

HRID 1917279Notes

Reaction equation

HRID 1917279 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH3:14][O:15][C:16](=[O:21])[C@@H:17]([CH3:20])[CH2:18][OH:19].O>CN(C)C=O>[CH3:14][O:15][C:16](=[O:21])[C@@H:17]([CH3:20])[CH2:18][O:19][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

Product 1

HCID 11128183methyl (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (13.3 g, 196 mmol) and tert-butyldimethylsilyl chloride (14.2 g, 94.1 mmol) were added to a solution of (S)-3-hydroxy-2-methylpropionic acid methyl ester (11.0 g, 93.1 mmol) in dimethylformamide (100 mL), and the mixture was stirred at room temperature for four hours. Water was added to the reaction mixture, followed by extraction with hexane twice. The extract was then dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to give 24 g (quantitative) of the title compound as a colorless oil.

Workup

  1. extractionfollowed by extraction with hexane twice
  2. dry with materialThe extract was then dried over magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a31d27dacb084750a1fecd404f622ee9
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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