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

HRID 654990Notes

Reaction equation

HRID 654990 reaction equation
[CH3:1][C@@H:2]([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].N1C=CN=C1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15]>C(OCC)(=O)C>[Si:18]([O:8][CH2:7][C@H:2]([CH3:1])[C:3]([O:5][CH3:6])=[O:4])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl (S)-(+)-2-methyl-3-hydroxypropionate (1.0 g; 8.47 mmole) and imidazole (1.15 g; 16.9 mmole) were dissolved in dry dimethylfofmamide (10 ml), t-butyl dimethylchlorosilane (1.30 g; 8.62 mmole) was added thereto, and the resultant mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (60 ml), washed with an aqueous sodium chloride solution (50 ml) three times and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give methyl (S)-3-t-butyldimethylsilyloxy-2-methylpropionate

Workup

  1. additionwas added
  2. washwashed with an aqueous sodium chloride solution (50 ml) three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9a4e432fb326436aa2a12a3a39f24876
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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