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

HRID 2259223Notes

Reaction equation

HRID 2259223 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-16a7c77ecd4d4c438af8cdc3534796a5
Source dataset
uspto-grants-1995_12
Patent number
US05472959

Reaction notes

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