4,4'-Difluorobenzophenone → HCID 15133032, compound

HRID 1086085Notes

Reaction equation

C([Li])CCC.C(NC1CCCCC1)(C)C.[CH:16]1([CH2:19][C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH2:18][CH2:17]1.[F:27][C:28]1[CH:42]=[CH:41][C:31]([C:32]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)=[O:33])=[CH:30][CH:29]=1>O1CCCC1>[CH:16]1([CH:19]([C:32]([C:31]2[CH:41]=[CH:42][C:28]([F:27])=[CH:29][CH:30]=2)([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[OH:33])[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH2:17][CH2:18]1

Participants

Conditions

Temperature: -70 °C

Procedure

Butyl lithium (5 mL of 2M solution, 10 mmol) was added to a solution of N-isopropylcyclohexylamine(1.4 g, 10 mmol) in 20 mL of tetrahydrofuran at -10° C. After stirring for 30 minutes and cooling to -70° C., butyl cyclopropaneacetate (1.5 g 10 mmol) was added. After stirring for an additional 30 minutes, 4,4'-difluorobenzophenone (1.1 g, 5 mmol) was added and the mixture stirred for 6 hours at -70° C. The mixture was quenched with 2N hydrochloric acid and extracted with diethyl ether. The extracts were dried and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 0.75% ethyl acetate in hexane to give 1.0 g of the title compound; m.p. =77°-80° C.

Workup

stirringAfter stirring for an additional 30 minutes
stirringthe mixture stirred for 6 hours at -70° C
customThe mixture was quenched with 2N hydrochloric acid
extractionextracted with diethyl ether
customThe extracts were dried
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica eluting with 0.75% ethyl acetate in hexane

Sources & evidence

ORD record: ord-1dd47a5deff24507995ba98857b74c56
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011947

Reaction notes

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