[H-].[Na+].[OH:3][CH2:4][C:5]([CH3:9])([CH3:8])[C:6]#[N:7].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCCCCC.CN(C=O)C.O>[CH2:10]([O:3][CH2:4][C:5]([CH3:9])([CH3:8])[C:6]#[N:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
A solution of 60% sodium hydride (367.1 mg, 15.3 mmol) was washed with hexane (3×2 mL) and suspended in DMF (2 mL). The suspension was cooled to -10° C. and then a mixture of 3-hydroxy-2,2-dimethylpropanenitrile (1.4 g, 13.9 mmol) and DMF (8 mL) was added. The mixture was cooled 2.5 hour with stirring stirred at -10° to -5° C. and then benzyl bromide (1.7 mL, 13.9 mmol) was added. The mixture was cooled 2 hours with stirring at -5° C., diluted with water (10 mL) and extracted with diethyl ether (3×10 mL). The combined extracts were washed with water (1×10 mL) and brine (1×10 mL), dried (MgSO4) and concentrated to give 3-benzyloxy-2,2-dimethylpropanenitrile (2.5 g, 13.2 mmol).
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