4-Chlorophenyl cyclopropyl ketone → 1-(4-Chlorophenyl)-1-cyclopropyl-2-propen-1-ol
Reaction equation
[CH:1]([Mg]Br)=[CH2:2].[CH:5]1([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6]1>O1CCCC1>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]([CH:5]2[CH2:6][CH2:7]2)([OH:9])[CH:1]=[CH2:2])=[CH:15][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
A 1.0 M solution of vinylmagnesium bromide in tetrahydrofuran (110 mL, 0.11 mole) was stirred, and a solution of 18.1 grams (0.1 mole) of commercially available 4-chlorophenyl cyclopropyl ketone in 50 mL of dry tetrahydrofuran was added dropwise during a one hour period. The exothermic reaction caused the reaction mixture to warm to 45° C. Upon completion of addition, the reaction mixture was stirred for two hours as it cooled to ambient temperature. The reaction was quenched with the addition of 50 mL of a saturated, aqueous solution of ammonium chloride. The mixture was extracted with two 50 mL portions of diethyl ether. The combined extracts were dried with potassium carbonate and filtered. The filtrate was concentrated under reduced pressure, yielding 20.0 grams of 1-(4-chlorophenyl)-1-cyclopropyl-2-propen-1-ol.
Workup
- customThe exothermic reaction
- additionUpon completion of addition
- temperaturecooled to ambient temperature
- customThe reaction was quenched with the addition of 50 mL of a saturated, aqueous solution of ammonium chloride
- extractionThe mixture was extracted with two 50 mL portions of diethyl ether
- dry with materialThe combined extracts were dried with potassium carbonate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e78e86f079834794837be085a611ea67
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808762
Reaction notes
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