Imidazole → methyl (t-butyldimethylsilyloxy)acetate

HRID 964332Notes

Reaction equation

HRID 964332 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].[CH3:7][C:8]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])[CH3:9].N1C=CN=C1.O>CN(C)C=O>[Si:11]([O:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])([C:8]([CH3:10])([CH3:9])[CH3:7])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 66774Methyl Glycolate

Product 1

HCID 11171734methyl (t-butyldimethylsilyloxy)acetateYield 97,876,664%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl glycolate (0.776 ml, 0.905 g, 10.0 nmol) was added to a suspension of TBDMS-Cl (1.81 g, 12.0 mmol) and imidazole (1.7 g, 25.0 mmol) in dry dimethylformamide (DMF) (2.0 ml) at 0° C., under stirring. After 90 min stirring at RT, water (25 ml) was added, and the resulting mixture was extracted with ethyl ether (3×15 ml). The organic phases were combined, washed with water (3×15 ml), dried (Na2SO4) and evaporated to give methyl (t-butyldimethylsilyloxy)acetate (2.0 g, 100%).

Workup

  1. stirringAfter 90 min stirring at RT
  2. extractionthe resulting mixture was extracted with ethyl ether (3×15 ml)
  3. washwashed with water (3×15 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7cf9a88370b5437eacec6c295dbdd33b
Source dataset
uspto-grants-1998_06
Patent number
US05767282

Reaction notes

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