4-Chlorophenyl cyclopropyl ketone → 1-[1-(p-Chlorophenyl)-2-methoxyvinyl]cyclopropane
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH:29]1([C:32]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=O)[CH2:31][CH2:30]1>CCOCC>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C:32]([CH:29]2[CH2:31][CH2:30]2)=[CH:2][O:3][CH3:4])=[CH:35][CH:36]=1Participants
Conditions
- Temperature
- 2.5 °C
Procedure
A solution of methoxymethyl triphenyl phosphonium chloride (20.5 g, 0.060 mol) in ether is cooled to -60° C., treated with a 2.5M solution of butyllithium in hexanes (25.2 mL, 0.063 mol), warmed to and stirred at 0-5° C. for 90 minutes, recooled to -60° C., treated with a solution of 4-chlorophenyl cyclopropyl ketone (9.03 g, 0.050 mol) in ether, warmed to and stirred at room temperature overnight, quenched with ethyl acetate and 2N hydrochloric acid, and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 2N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (1:9) gives the title product as an oil (6.2 g, 60%).
Workup
- temperaturewarmed to and
- customrecooled to -60° C.
- temperaturewarmed to and
- stirringstirred at room temperature overnight
- customquenched with ethyl acetate and 2N hydrochloric acid
- extractionextracted with ethyl acetate
- washwashed sequentially with water, 2N hydrochloric acid and water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto obtain a residue
Sources & evidence
- ORD record
- ord-eee5c3742f254ec3b383a988b5b6bc1f
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998673
Reaction notes
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