2-Cyclohexen-1-one, 3-methoxy-5,5-dimethyl- → 2-Cyclohexenone, 5,5-dimethyl-
Reaction equation
C[O:2][C:3]1[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5](=O)[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:9][C:7]1([CH3:10])[CH2:8][C:3](=[O:2])[CH:4]=[CH:5][CH2:6]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-methoxy-5,5-dimethyl-cyclohex-2-enone (80 g, 0.52 mol) in anhydrous tetrahydrofuran (270 mL) was treated dropwise with a 1 M solution of LiAlH4 in tetrahydrofuran (182 mL), under argon atmosphere and keeping the temperature of the reaction between 0° C. and 5° C. The temperature was allowed to rise to 25° C. and the mixture was stirred for 4 hours. The resulting slurry was cooled with an ice bath, quenched with ethyl acetate (30 mL) and poured with caution into a cooled 2 M H2SO4 solution. The aqueous solution was then extracted with diethyl ether (300 mL×3), dried on Na2SO4 and evaporated under reduced pressure to remove most of the solvent. The crude material contained the title compound as a low boiling point oil that was used in the next step without further purification.
Workup
- customthe temperature of the reaction between 0° C. and 5° C
- customto rise to 25° C.
- temperatureThe resulting slurry was cooled with an ice bath
- customquenched with ethyl acetate (30 mL)
- additionpoured with caution into a cooled 2 M H2SO4 solution
- extractionThe aqueous solution was then extracted with diethyl ether (300 mL×3)
- customdried on Na2SO4
- customevaporated under reduced pressure
- customto remove most of the solvent
- customwas used in the next step without further purification
Sources & evidence
- ORD record
- ord-f0023faa098d4f81b7daacf8f92ff27c
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08981089B2
Reaction notes
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