Hydrochloric Acid → 5-Hydroxy-4,4-dimethyl-3-oxopentanenitrile

Participants

Reaction Steps

To a refluxing suspension of sodium hydride (1.40 g of a 60% suspension in mineral oil, 35 mmol) in anhydrous toluene (45 mL), was added dropwise (over 1 h) a mixture of methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate (6.0 g, 24.39 mmol) from Step A and acetonitrile (1.80 mL, 35 mmol). After refluxing for a further 5 h, the mixture was cooled to rt and the pH was adjusted to 4 with aqueous HCl solution. The mixture was extracted with ethyl acetate (3×200 mL) and the combined organic layers washed with brine (2×200 mL), separated, dried over Na2SO4, and filtered. Concentration under reduced pressure, followed by Purification via silica gel chromatography eluting with 33% ethyl acetate in petroleum ether, afforded 5-hydroxy-4,4-dimethyl-3-oxopentanenitrile as a yellow oil (1 g, 29%). 1H NMR (300 MHz, CDCl3) δ 3.76 (s, 2H), 3.61 (s, 2H), 1.19 (s, 6H).

Provenance & Evidence