Diethyl Ether → 1-Cyano-2-[(3-methoxyphenyl)methyl]cyclohexane
Reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[CH:12]=[CH:13][CH:14]=1.C1(C)C=CC(S([CH2:32][N+:33]#[C-])(=O)=O)=CC=1.C(OCC)C>C(O)(C)(C)C.COCCOC.COCCOC.O>[C:32]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH3:7])[CH:10]=1)#[N:33]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of potassium tert-butoxide (4.10 g) in tert-butanol-1,2-dimethoxyethane (1:1, 38 ml) was added dropwise to a stirred solution of 2-[(3-methoxyphenyl)-methyl]cyclohexanone (4.10 g) and (p-tolylsulfonyl)methyl isocyanide (4.10 g) in 1,2-dimethoxyethane under ice cooling over 30 minutes. The resulting mixture was stirred at the same temperature for 1 hour and at room temperature for 2 hours and 30 minutes, and then a mixture of diethyl ether and water was added thereto. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed over silica gel using n-hexane--ethyl acetate as an eluent to afford 1-cyano-2-[(3-methoxyphenyl)methyl]cyclohexane (3.73 g) as an oil.
Workup
- additionwas added
- customThe organic layer was separated
- washwashed with water and brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe oily residue was chromatographed over silica gel
Sources & evidence
- ORD record
- ord-8fc6da633c114998b50b57fe3fdebd3a
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06025375
Reaction notes
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