Benzenepropanoic acid → tert-Butyl(dimethyl)silyl 3-phenylpropanoate

HRID 260653Notes

Reaction equation

HRID 260653 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1.C(OCC)C>CN(C)C=O.O>[C:1]1([CH2:7][CH2:8][C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 107Benzenepropanoic acidHCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 554838tert-Butyl(dimethyl)silyl 3-phenylpropanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve 3-phenylpropionic acid (1.5 g, 10 mmol) in dimethylformamide (5 mL) and add t-butyldimethylsilyl chloride (7.5 g, 50 mmol) and imidazole (6.8 g, 0.1 mol). Stir for 48 hours at room temperature, pour into ethyl ether and water and separate the organic phase. Dry (MgSO4) and evaporate the solvent in vacuo to give 3-phenylpropionic acid, t-butyldimethylsilyl ester.

Workup

  1. customseparate the organic phase
  2. dry with materialDry (MgSO4)
  3. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-e1e940715b1748ba88edcfbf2c895295
Source dataset
uspto-grants-1996_06
Patent number
US05529997

Reaction notes

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