Diethyl Carbonate → Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

HRID 705333Notes

Reaction equation

[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.CC(C)([O-])C.[K+].[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[O:17]>C1(C)C=CC=CC=1>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:16](=[O:17])[CH2:15][C:1]([O:5][CH2:6][CH3:7])=[O:8])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 78 °C

Procedure

Diethyl carbonate (801 mL, 6.79 mole) was added dropwise over a 30 minute period to a stirring slurry of potassium t-butoxide (609.2 g, 5.43 mole) in toluene (9.5 L) under a nitrogen atmosphere. The reaction mixture was heated to 78° C. and 4-fluoroacetophenone (250 g, 1.81 mole) in toluene (250 mL) was added over a one hour time period. Heating of the reaction mixture was continued overnight. Then the reaction mixture was quenched with 1.5 N HCl(aq) and extracted with ethyl acetate (3×1 L). The combined organic extracts were washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo leaving a brown liquid. The liquid was distilled to give the title compound as a colorless liquid (250 g, 79%). MS m/z 209 (M−H)−.

Workup

temperatureHeating of the reaction mixture
customThen the reaction mixture was quenched with 1.5 N HCl(aq)
extractionextracted with ethyl acetate (3×1 L)
washThe combined organic extracts were washed with saturated sodium bicarbonate
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customleaving a brown liquid
distillationThe liquid was distilled

Sources & evidence

ORD record: ord-efcde0541db14c3c9776be1fbf74baf7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173887B2

Reaction notes

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