O-ethylhydroxylamine hydrochloride → 3-[1-(Ethoxyimino)butyl]-4-hydroxy-9-methyl-1-oxaspiro[5.5]undec-3-en-2-one

Participants

Reaction Steps

The acylated compound (8.20) (1.00 g, 3.75 mmol) was oximated with ethoxyamine hydrochloride (0.39 g, 4.0 mmol) in the presence of triethylamine as described in Part (c) of the general procedure above, to afford the title compound (4.9) (1.00 g, 86%) as a mobile pale yellow oil. (Found: M, 309.196. C17H27NO4 requires 309.194.) 1H n.m.r. δ (CDCl3) 14.80, very broad s, 1H; 4.08, q, J 7 Hz, OCH2CH3 ; 3.00, t, J 7.5 Hz, CH2CH2CH3 ; 2.68, s, 2H5; 2.2-1.2 complex, 11H; 1.30, t, J 7.5 Hz, OCH2CH3 ; 1.15-0.7, m, CH2CH2CH3 & CH3.

Provenance & Evidence