Potassium trimethylsilanolate → 3-[1-[2-(4-Chlorophenyl)ethyl]-3-oxo-3-phenylpropyl]-benzoic acid

HRID 1647231Notes

Reaction equation

HRID 1647231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25]C)=[O:24])[CH2:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C[Si](C)(C)[O-].[K+]>C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([OH:25])=[O:24])[CH2:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 867487633-[1-[2-(4-Chlorophenyl)ethyl]-3-oxo-3-phenylpropyl]benzoic acid, methyl ester

Product 1

HCID 199264943-[1-[2-(4-Chlorophenyl)ethyl]-3-oxo-3-phenylpropyl]-benzoic acidYield 62.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-[1-(2-(4-Chlorophenyl)ethyl]-3-oxo-3-phenylpropyl]-benzoic acid, methyl ester (0.5 g, 1.22 mmol) is dissolved in diethyl ether (100 mL) and treated with potassium trimethylsilanolate (1 g, 7.8 mmol). After the mixture is stirred 18 hours, the resulting solid is collected by filtration and washed with diethyl ether. The dried cake is dissolved in water, acidified with 1N hydrochloric acid, and the resulting solid collected by filtration. Crystallization in diethyl ether-hexane provides 0.3 g of the title compound as large cottony needles; mp 93°-95° C.

Workup

  1. filtrationthe resulting solid is collected by filtration
  2. washwashed with diethyl ether
  3. dissolutionThe dried cake is dissolved in water
  4. filtrationthe resulting solid collected by filtration
  5. customCrystallization in diethyl ether-hexane

Sources & evidence

ORD record
ord-9620c193991f436c8d8e624539129c00
Source dataset
uspto-grants-1995_07
Patent number
US05430047

Reaction notes

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