1,5-Diphenylpentan-3-one → Methyl formate

HRID 1779277Notes

Reaction equation

HRID 1779277 reaction equation
[CH3:1][O-:2].[Na+].[C:4]1([CH2:10][CH2:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(OCC)C>[C:15]1([CH2:14][CH2:13][C:12](=[O:21])[CH2:11][CH2:10][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH:1]([O:21][CH3:12])=[O:2]

Participants

5

Reactant 2

HCID 214961,5-Diphenylpentan-3-oneHCID 10942334Sodium Methoxide

Product 2

HCID 7865Methyl formateYield 220%HCID 214961,5-Diphenylpentan-3-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of sodium methoxide (6 g) in ethylether (80 ml), a mixture of 1,5-diphenyl-3-pentanone (24 g, 0.1 mole) obtained in above (1) and methyl formate (6.7 g, 0.11 mole) was added dropwise at 1°-2° C., stirring was continued for 1 hour at the same temperature and allowed to stand overnight at room temperature. The reaction mixture was poured into cold H2O (300 ml), and aqueous layer was separated, acidified to ph 1 with 5% sulfuric acid and extracted with ethylether (100 ml×3). The organic layer was separated, washed with H2O (100 ml×2), dried over anhydrous MgSO4 and evaporated to give 12.7 g of the title compound as a pale yellow oil. The product was found to have keto-form and enol-form in molar ratio of ca. 1:1 based on 1HNMR.

Sources & evidence

ORD record
ord-3c017091bfc84794a90caffda00d5a3b
Source dataset
uspto-grants-1997_05
Patent number
US05627006

Reaction notes

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