Water → Benzyl 5-(1-hydroxysilinan-1-yl)pentanoate

Participants

Reaction Steps

To crude benzyl 5-(1-chlorosilinan-1-yl)pentanoate (400 mg, 1.23 mmol) 1 N aqueous sodium hydroxide (0.3 mL, 0.3 mmol) was added and the contents sonicated for 10 minutes. After this time, the reaction was diluted with water (1 mL) and sonicated for 5 minutes. After this time, the reaction mixture was diluted further with water (10 mL) and ethyl acetate (25 mL). The organic layer was separated from the aqueous layer, and the aqueous layer was back extracted with ethyl acetate (2×25 mL). The combined organics were dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography eluting with hexanes to 1:4 ethyl acetate/hexanes over 40 minutes to afford benzyl 5-(1-hydroxysilinan-1-yl)pentanoate (209 mg, 55%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.38-7.27 (m, 5H), 5.10 (s, 2H), 2.74 (bs, 1H), 2.39-2.29 (m, 2H), 1.76-1.57 (m, 6H), 1.48-1.30 (m, 4H), 0.72-0.47 (m, 6H).

Provenance & Evidence