Methyl iodide → 2-(4-Methoxyphenyl)-2-methylpropanenitrile
Reaction equation
[CH:1]([N-:4]C(C)C)(C)C.[Li+].COC1C=CC(CC#N)=CC=1.IC.[Cl-].[NH4+].CCCCCCC.[CH2:31]1[CH2:35][O:34][CH2:33][CH2:32]1.[CH2:36]([C:38]1[CH:43]=[CH:42][CH:41]=C[CH:39]=1)C>C1COCC1>[CH3:33][O:34][C:35]1[CH:31]=[CH:32][C:43]([C:38]([CH3:36])([CH3:39])[C:1]#[N:4])=[CH:42][CH:41]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of lithium diisopropylamide (2M; 61.1 ml; 122.3 mmol;) in heptane/THF/ethylbenzene was cooled in an ice bath and treated dropwise, under nitrogen, with a solution of (4-methoxy-phenyl)acetonitrile (6.0 g; 40.77 mmol) in 30 ml of THF. After stirring for 45 minutes at 0C, iodomethane (12.69 ml; 203.85 mmol) was added and the mixture stirred at rt for 12 hours. The reaction mixture was added to a saturated solution of ammonium chloride (300 ml) and extracted twice with ethyl acetate (200 ml). The organic phase was washed once with saturated brine (100 ml), dried over sodium sulfate and concentrated to dryness. Purification by flash chromatography on silica gel using an ethyl acetate/hexane gradient (5–30%) afforded 2-(4-methoxyphenyl)-2-methylpropanenitrile (6.0 g; 84% yield).
Workup
- additionwas added
- extractionextracted twice with ethyl acetate (200 ml)
- washThe organic phase was washed once with saturated brine (100 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated to dryness
- customPurification by flash chromatography on silica gel using an ethyl acetate/hexane gradient (5–30%)
Sources & evidence
- ORD record
- ord-daa33f2339cb420fbc0971cf423d19c1
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07319104B2
Reaction notes
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