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

HRID 375794Notes

Reaction equation

HRID 375794 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-13b434cbf37c4ca2bf8a50495c7064bf
Source dataset
uspto-grants-1996_01
Patent number
US05488047

Reaction notes

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