Acrylonitrile → 2-(1,1-Dimethylethyl)-5-hydroxy-4-pyridinecarbonitrile
Reaction equation
[CH3:1][C:2]([C:5]1O[C:7]([O:10]CC)=[CH:8][N:9]=1)([CH3:4])[CH3:3].[C:13](#[N:16])[CH:14]=[CH2:15]>>[C:13]([C:14]1[CH:15]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:9]=[CH:8][C:7]=1[OH:10])#[N:16]Participants
3
Conditions
- Temperature
- 20 °C
Procedure
A neat mixture of 2-(1,1-dimethylethyl)-5-ethoxyoxazole (17 g., 0.1 mole) and acrylonitrile (6.1 g., 0.11 mole) is stirred and heated at 70°-75° C. for 16 hours. The resulting dark reaction mixture is cooled to 20° C. and chromatographed on silica gel (600 g.). Elution with 1% methanol in chloroform (4.35 l.) yields recovered 2-(1,1-dimethylethyl)-5-ethoxyoxazole (10.7 g., 63% recovery). Continued elution with the same eluant (300 ml.) affords impure product (3.2 g.). Further elution with the same eluant (2.5 l.) gives the desired product as a solid (6.5 g., 37%), m.p. 185°-195° C. Two recrystallizations of the latter from methanol-water (1:1; v:v) provides an analytical sample of 4-cyano-6-(1,1-dimethylethyl)-3-pyridinol as colorless crystals (4.5 g., 26%), m.p. 201°-202° C.