Imidazole → Ethyl 4-cyano-3-(tert-butyldiphenylsilyloxy)-butanoate

HRID 226273Notes

Reaction equation

HRID 226273 reaction equation
N1C=CN=C1.[C:6]([CH2:8][CH:9]([OH:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:7].[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18].O>ClCCl>[C:6]([CH2:8][CH:9]([O:16][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 4184461Ethyl 4-cyano-3-hydroxybutanoate

Product 1

HCID 11718177Ethyl 4-cyano-3-(tert-butyldiphenylsilyloxy)-butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (6.5 g, 0.095 mol) was added to a chilled solution (−5 to −10° C.) of ethyl 4-cyano-3-hydroxybutanoate (10 g, 0.063 mol) in dichloromethane (100 ml) under stirring, followed by tert-butyl diphenyl silyl chloride (15.7 g, 0.057 mol). After stirring for 4 hours at room temperature, water (250 ml) was added to the reaction mixture and layers separated. The aqueous layer was extracted with dichloromethane (100 ml) and combined with the organic layer. The combined organic layer was evaporated to give title compound.

Workup

  1. stirringAfter stirring for 4 hours at room temperature
  2. customseparated
  3. extractionThe aqueous layer was extracted with dichloromethane (100 ml)
  4. customThe combined organic layer was evaporated

Sources & evidence

ORD record
ord-e26669bfbe024d138ddc363d0ea73067
Source dataset
uspto-grants-2009_07
Patent number
US07557238B2

Reaction notes

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