The general procedure for the synthesis of 3-hydroxy-2,2-dimethylpropionitrile from ethyl 2-cyano-2-methylpropionate was as follows:
1) Dissolve ethyl 2-cyano-2-methylpropionate (5.0 g, 35.4 mmol) in a solvent mixture of tetrahydrofuran (40 mL) and water (100 mL).
2) Sodium borohydride (4.47 g, 106 mmol) was added slowly and the reaction mixture was stirred at room temperature for 3 hours.
3) Upon completion of the reaction, 6N hydrochloric acid was slowly added to the mixture to quench the reaction.
4) The reaction mixture was extracted with ethyl acetate and the organic phases were combined.
5) The organic phase was washed with water, dried over anhydrous magnesium sulfate, filtered and passed through a small amount of silica gel column.
6) The filtrate was concentrated under pressure to give the title compound 3-hydroxy-2,2-dimethylpropionitrile (3.4 g, 97% yield) as an oil.
The product was characterized by 1H-NMR (CDCl3): δ 1.36 (6H, s), 3.58 (2H, s).
