Methyl iodide → 2-[(2-Methoxyphenyl)(1-naphthyl)methyl]-2-methylmalononitrile
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH:10]([C:13]#[N:14])[C:11]#[N:12].[CH3:25]I>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[C:10]([CH3:25])([C:13]#[N:14])[C:11]#[N:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -35 °C
Procedure
2-[(2-Methoxyphenyl)(1-naphthyl)methyl]malononitrile of Example 1 (196 mg, 0.63 mmol) was dissolved in 10 mL of tetrahydrofuran and cooled to −35° C. Potassium hexamethyldisilyl amide (1.14 mL, 0.75 mmol, 0.66 M in toluene) was added. The cooling bath was removed, and the reaction allowed to warm to room temperature, after which methyl iodide (0.078 mL, 125 mmol) was added. The reaction mixture was stirred 30 minutes, then quenched with 1 N hydrochloric acid and taken up in ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, brine, dried over mgnesium sulfate, filtered, and evaporated to dryness. Following purification on silica (20% ethyl acetate/hexanes) and recrystallization from methanol, 104 mg product was isolated as a crystalline solid, mp 175-177° C.
Workup
- customThe cooling bath was removed
- temperatureto warm to room temperature
- customquenched with 1 N hydrochloric acid
- washThe organic layer was washed with saturated aqueous sodium bicarbonate, brine
- dry with materialdried over mgnesium sulfate
- filtrationfiltered
- customevaporated to dryness
- custompurification
- customon silica (20% ethyl acetate/hexanes) and recrystallization from methanol
Sources & evidence
- ORD record
- ord-609f3c674a6846bea66d78748e7896d9
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425580B2
Reaction notes
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