Imidazole → ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate

HRID 2255664Notes

Reaction equation

HRID 2255664 reaction equation
N1[CH:5]=[CH:4]N=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH2:14].[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16].[CH3:21]N(C)C=O>>[Si:6]([O:14][C@@H:4]([C:16](=[CH2:21])[C:15]([O:18][CH2:19][CH3:20])=[O:17])[CH3:5])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11108029ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate

Procedure

To a suspension of ethyl 2-[(1R)-1-hydroxyethyl]acetylate (11.22 g) and imidazole (6.89 g) in N,N-dimethylformamide (110 ml) was added portionwise t-butyldimethylsilyl chloride (14.08 g) at 0° C. After the mixture was stirred for 10 hours, the reaction mixture was poured into a mixture of water and ethyl acetate. The water layer was separated and extracted twice with ethyl acetate. The combined organic layers were washed with water, 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and an aqueous sodium chloride, and then, dried over magnesium sulfate. The resultant solution was evaporated, and the residue was distilled to give ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-acrylate (19.53 g).

Workup

  1. customThe water layer was separated
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with water, 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water
  4. dry with materialan aqueous sodium chloride, and then, dried over magnesium sulfate
  5. customThe resultant solution was evaporated
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-15d52d5967614e998c0079f2bad0ff8d
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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