Methanol → 2-(2,2-Dimethoxyethyl)nicotinonitrile
Reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10])(C)C.[CH3:15][O-:16].[Na+].[CH3:18][OH:19]>>[CH3:15][O:16][CH:5]([O:19][CH3:18])[CH2:6][C:7]1[N:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-((trimethylsilyl)ethynyl)nicotinonitrile (19.14 g, 95.7 mmol) in MeOH (200 mL) was added sodium methanolate (16.5 g, 306.2 mmol). The reaction mixture was refluxed at 80° C. for 14 h under N2. After removal of the MeOH, the residue was diluted with H2O and extracted with DCM (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluting with DCM) to yield 2-(2,2-dimethoxyethyl)nicotinonitrile as a yellow oil (13.76 g, yield 75%). ESI MS: m/z 193 [M+H]+.