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

HRID 2255659Notes

Reaction equation

HRID 2255659 reaction equation
[OH:1][CH:2]([C:4](=[CH2:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:3].N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C)C=O.C(OCC)(=O)C>[Si:16]([O:1][CH:2]([C:4](=[CH2:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:3])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 10855587Butanoic acid, 3-hydroxy-2-methylene-, ethyl ester

Product 1

HCID 14634473Ethyl 2-[1-(t-butyldimethylsilyloxy)ethyl]acrylateYield 95.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of ethyl 2-(1-hydroxyethyl)acrylate (40 g) and imidazole (28.3 g) in N,N-dimethylformamide (200 ml)was added portionwise t-butyldimethylsilyl chloride (46 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 aqueous 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 in turn, and then dried over magnesium sulfate. The evaporation of the solution gave ethyl 2-[1-(t-butyl-dimethylsilyloxy)ethyl]acrylate (68.5 g).

Workup

  1. customThe aqueous 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 in turn, and then dried over magnesium sulfate
  5. customThe evaporation of the solution

Sources & evidence

ORD record
ord-03f7eb77e5134ab59f6b5a9ed537e78c
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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