4-Chlorophenyl cyclopropyl ketone → 1-(4-Chlorophenyl)-1-cyclopropyl-2-propen-1-ol

HRID 1588887Notes

Reaction equation

HRID 1588887 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:8][CH:7]=1>O1CCCC1>[CH:14]1([C:12]([C:9]2[CH:8]=[CH:7][C:6]([Cl:5])=[CH:11][CH:10]=2)([OH:13])[CH:1]=[CH2:2])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 811484-Chlorophenyl cyclopropyl ketoneHCID 178418507HCID 178418507, compound

Product 1

HCID 150420331-(4-Chlorophenyl)-1-cyclopropyl-2-propen-1-olYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 73 ml (0.073 mole) of 1 M vinylmagnesium bromide in tetrahydrofuran was cooled in an ice water bath, and a solution of 11.0 grams (0.061 mole) of cyclopropyl 4-chlorophenyl ketone in 20 ml of tetrahydrofuran was added dropwise. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for about 18 hours. After this time the reaction was quenched by the addition of 100 ml of aqueous 10% hydrochloric acid. The reaction mixture was stirred for 10 minutes and then was extracted with two 50 ml portions of diethyl ether. The combined extracts were washed with 10 ml of water and then were dried with magnesium sulfate. The mixture was filtered through a pad of silica gel, and the filtrate was concentrated under reduced pressure, yielding 11.0 grams of 1-cyclopropyl-1-(4-chlorophenyl)-2-propen-1-ol.

Workup

  1. additionUpon completion of addition
  2. customAfter this time the reaction was quenched by the addition of 100 ml of aqueous 10% hydrochloric acid
  3. stirringThe reaction mixture was stirred for 10 minutes
  4. extractionwas extracted with two 50 ml portions of diethyl ether
  5. washThe combined extracts were washed with 10 ml of water
  6. dry with materialwere dried with magnesium sulfate
  7. filtrationThe mixture was filtered through a pad of silica gel
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d8bd89e59e140849fa4b2d5ad8b87e5
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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