16733-97-4 → HCID 15411269, compound

HRID 2293293Notes

Reaction equation

[Li+].[CH-:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[F:7][C:8]1[CH:25]=[CH:24][C:11]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=O)=[CH:10][CH:9]=1>O1CCCC1>[C:2]1(=[C:12]([C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:25][CH:24]=2)[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3]1

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of 3.7 g (50 mmol) of lithium cyclopentadienylide in 90 ml of anhydrous tetrahydrofuran is added to a solution of 11.1 g (40 mmol) of 4-fluoro-4'-methylsulfonylbenzophenone, prepared in Example 2, in 70 ml of anhydrous tetrahydrofuran, cooled to 10° C. The reaction medium is stirred for 2 hours at this temperature and then for 24 hours at room temperature. It is subsequently poured onto ice. After dilution with water, the mixture is extracted with t-butyl methyl ether. The organic phase is dried over magnesium sulfate and then concentrated in the cold. The residue obtained is chromatographed on silica gel in dichloromethane. The resulting oil crystallizes from a petroleum ether/t-butyl methyl ether mixture to give 3.6 g of 4-[(cyclopenta-2,4-dienylidene)(4-fluorophenyl)methyl]methylsulfonylbenzene in the form of orange crystals melting at 110° C.

Workup

waitfor 24 hours at room temperature
additionIt is subsequently poured onto ice
extractionAfter dilution with water, the mixture is extracted with t-butyl methyl ether
dry with materialThe organic phase is dried over magnesium sulfate
concentrationconcentrated in the cold
customThe residue obtained
customis chromatographed on silica gel in dichloromethane
customThe resulting oil crystallizes from a petroleum ether/t-butyl methyl ether mixture

Sources & evidence

ORD record: ord-64e0f063467a4003abfe119244e160e4
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686460

Reaction notes

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