Water → 1-(p-Chlorophenyl)-1-[2-fluoro-3-(m-phenoxyphenyl)propenyl]cyclopropane

HRID 1741429Notes

Reaction equation

C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([CH:22](O)[C:23]([F:41])([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:29]=3)C(O)=O)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1.O>N1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([CH:22]=[C:23]([F:41])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:29]=3)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

p-Toluenesulfonyl chloride (19.07 mg, 0.10 mmol) is added to a solution of 1-(p-chlorophenyl)-α-fluoro-β-hydroxy-α-(m-phenoxybenzyl)cyclopropanepropionic acid having a 9:1 [R,S and S,R] to [R,R and S,S] ratio (20 mg, 0.05 mmol) in pyridine (2 mL). The reaction mixture is heated to 60° C. and poured into water. The aqueous mixture is extracted with diethyl ether. The organic extracts are combined, washed sequentially with 2 N hydrochloric acid, water, 10% sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a colorless oil (18 mg, 100%) which is found to have a 9:1 Z to E ratio by NMR spectral analyses.

Workup

extractionThe aqueous mixture is extracted with diethyl ether
washwashed sequentially with 2 N hydrochloric acid, water, 10% sodium hydrogen carbonate solution and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-12c4c7fecb4c481884cabdd10fa91287
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05973190

Reaction notes

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