Hydroxyamine hydrochloride → HCID 131720754, compound

Participants

Reaction Steps

A solution of the aldehyde, methyl 2-(1,1-dimethylethyl)-2-methyl-4-oxobutanoate (2.05 g, 11 mmol) and H2NOH.HCl (1.15 g, 16.5 mmol) in dry pyridine (10 mL) was stirred at 60° C. for 4 h in a nitrogen atmosphere. After cooling the reaction mixture was poured into ice cold HCl (3N, 50 mL), and extracted with ether (3×40 mL). The combined ether extract was washed sequentially with 40 mL portions of saturated NaHCO3, water, and brine, and dried over MgSO4. The solvent was removed in vacuo to give 2.30 g of pale brown colored viscous liquid. Flash chromatography over silica gel (hexanes-EtOAc, 4:1) followed by bulb-to-bulb distillation (pot temp. 100°-105° C. (0.4 mmHg)) afforded the anti- and syn- oxime mixture (2.03 g, 92%) in the ratio of 58/42 as a colorless viscous liquid.

Provenance & Evidence