Imidazole → Ethyl [(tert-butyldimethylsilyl)oxy]acetate

HRID 1491999Notes

Reaction equation

HRID 1491999 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].[C:8]([Si:12]([CH3:15])([CH3:14])Cl)([CH3:11])([CH3:10])[CH3:9].N1C=CN=C1>CN(C)C=O.CCOCC>[Si:12]([O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 12184Ethyl GlycolateHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11183578Ethyl [(tert-butyldimethylsilyl)oxy]acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 33.93 g of ethyl glycolate, 62.7 g of t-butyldimethylchlorosilane and 58.5 g of imidazole in 150 ml of dimethylformamide is stirred at room temperature for 15 h. The mixture is diluted with ether and washed with water (2×100 ml), brine, dried (MgSO4) and evaporated. The residue is distilled to give ethyl t-butyldimethylsilyloxyacetate, b.p. 100°-105° C. (14 mm/Hg).

Workup

  1. washwashed with water (2×100 ml), brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. distillationThe residue is distilled

Sources & evidence

ORD record
ord-6383864f3720450a8b9f066ec489e75e
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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