Potassium Carbonate → HCID 22261595, compound

HRID 1610281Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][CH:9]([C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 3-(4-fluorophenyl)-3-oxopropionate (20 g, 95.1 mmol), 4-fluorobenzyl bromide (18.0 g, 85.6 mmol), potassium carbonate (26.3 g, 0.19 mol) and acetonitrile (300 ml) was stirred at 60° C. for 2 hrs. The reaction solution was concentrated under reduced pressure, water (200 ml) was added, and the mixture was extracted with ethyl acetate (200, 100 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:toluene=1:1-1:5) to give ethyl 2-(4-fluorobenzyl)-3-(4-fluorophenyl)-3-oxopropionate (19.0 g, 63%) as an oil.

Workup

concentrationThe reaction solution was concentrated under reduced pressure, water (200 ml)
additionwas added
extractionthe mixture was extracted with ethyl acetate (200, 100 ml)
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:toluene=1:1-1:5)

Sources & evidence

ORD record: ord-d033ae26713640f78d1477f237592aba
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982348B2

Reaction notes

Loading…