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

HRID 2165330Notes

Reaction equation

HRID 2165330 reaction equation
[C:1]([C:6]1[C:7](=[O:19])[O:8][C:9]2([CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH2:13]2)[CH2:10][C:11]=1[OH:12])(=O)[CH2:2][CH2:3][CH3:4].Cl.[CH2:21]([O:23][NH2:24])[CH3:22]>C(N(CC)CC)C>[CH2:21]([O:23][N:24]=[C:1]([C:6]1[C:7](=[O:19])[O:8][C:9]2([CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH2:13]2)[CH2:10][C:11]=1[OH:12])[CH2:2][CH2:3][CH3:4])[CH3:22]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 178450304HCID 178450304, compound

Product 1

HCID 1360564283-[1-(Ethoxyimino)butyl]-4-hydroxy-9-methyl-1-oxaspiro[5.5]undec-3-en-2-oneYield 86.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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.

Sources & evidence

ORD record
ord-e6cd55fc15234d838def102d3961275f
Source dataset
uspto-grants-1990_07
Patent number
US04939278

Reaction notes

Loading…