Hydrochloric Acid → Methyl 1-allylcyclohexanecarboxylate
Reaction equation
[CH:1]1([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11](Br)[CH:12]=[CH2:13].CC(C)([O-])C.[K+].Cl>CN(C)C=O.O>[CH2:13]([C:1]1([C:7]([O:9][CH3:10])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:12]=[CH2:11]Participants
7
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methyl cyclohexylcarboxylate (1.42 g) and allyl bromide (3.02 g) in N,N-dimethylformamide (20 mL) was added potassium tert-butoxide (1.68 g, 15.0 mmol) under ice cooling. The solution was stirred at room temperature for 16 hours, at 50° C. for 8 hours and further at room temperature for 64 hours. Water and 3N hydrochloric acid were then added to the solution, and it was extracted with diethyl ether. The extract was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=97:3) to give the title compound (340 mg).
Workup
- extractionwas extracted with diethyl ether
- washThe extract was washed with water and saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=97:3)
Sources & evidence
- ORD record
- ord-babd89385a2046c38f7579c3b285f050
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375115B2
Reaction notes
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