Hydroxyamine hydrochloride → HCID 118621187, compound

Participants

Reaction Conditions

Reaction Steps

[(1-Cyclopropylpent-4-en-2-yl)oxy]acetaldehyde (C67) (17 g from the previous step, ≦83 mmol) was dissolved in a 2:1 mixture of ethanol and water (450 mL). Sodium acetate (41 g, 500 mmol) was added; after the reaction mixture had been stirred for 15 minutes, hydroxylamine hydrochloride (98%, 21 g, 300 mmol) was added. The reaction mixture was heated to 60° C. for 24 hours. The reaction mixture was concentrated under reduced pressure to remove ethanol and extracted with dichloromethane (3×140 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo at 22° C. Silica gel chromatography (Gradient: 0% to 20% ethyl acetate in petroleum ether) provided the product as a colorless oil. By 1H NMR analysis, this material consisted of a roughly 1:1 mixture of E and Z oxime isomers. Yield: 10 g, 55 mmol, 49.6% over two steps.

Provenance & Evidence