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 2.5 M 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 2 N hydrochloric acid, and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 2 N 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 2 N hydrochloric acid
- extractionextracted with ethyl acetate
- washwashed sequentially with water, 2 N hydrochloric acid and water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto obtain a residue
Sources & evidence
- ORD record
- ord-d253f11c1bbc4d2d8c63d5773785af98
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235754B1
Reaction notes
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