Water → 4-(4-Hydroxybutyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

4-(3-Butenyl)benzoniitrile (from step (i) above, 10.8 g, 69 mmol) was dissolved in dry THF (140 mL) and was cooled to 0° C. BH3-Me2S complex (20 mL, 2 M) was added dropwise over 45 minutes at 0° C. and, after 7 hours, water (70 mL) and NaBO3-4H2O (25 g) were added and the mixture was stirred overnight before dilution with ether (700 mL) and brine (satd., 250 mL). After separation, the aqueous phase was extracted with ether (2×200 mL) and the combined extracts were dried, filtered and evaporated to give crude sub-title compound. Purification by flash chromatography on SiO2 (300 g) with heptane:EtOAc (3:1 to 1:1) gave the sub-title compound (6.99 g).

Provenance & Evidence