Ethyl Propionate → HCID 15133037, compound

HRID 1086070Notes

Reaction equation

C([Li])CCC.C(NC1CCCCC1)(C)C.[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:17][CH3:18].[F:23][C:24]1[CH:38]=[CH:37][C:27]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[O:29])=[CH:26][CH:25]=1>O1CCCC1>[F:23][C:24]1[CH:38]=[CH:37][C:27]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)([OH:29])[CH:17]([CH3:18])[C:16]([O:20][CH2:21][CH3:22])=[O:19])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: -40 °C

Procedure

Butyl lithium (8.6 mL of 2.1M solution, 18 mmol) was added to a solution of N-isopropylcyclohexylamine (2.8 g, 20 mmol) in 20 mL tetrahydrofuran at -5° C. After stirring for 30 minutes and further cooling to -40° C., ethyl propionate (2.0 g, 20 mmol) was added and the solution stirred for 0.5 hr. After further cooling to -60° C., 4,4'-difluorobenzophenone (2.2 g, 10 mmol) was added and the solution stirred for 2 hours at -60 to -40° C. and for another 2 hours at -15° C. The reaction was quenched with 2N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from petroleum ether to give 1.95 g of the title compound as a white solid; m.p. =38°-40° C.

Workup

stirringthe solution stirred for 0.5 hr
temperatureAfter further cooling to -60° C.
stirringthe solution stirred for 2 hours at -60 to -40° C. and for another 2 hours at -15° C
customThe reaction was quenched with 2N hydrochloric acid
extractionthe mixture extracted with diethyl ether
dry with materialThe extracts were dried with magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record: ord-03d863fa1c4f40db9125c77e2220b756
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011947

Reaction notes

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