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

HRID 1534027Notes

Reaction equation

HRID 1534027 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 and CH3.

Sources & evidence

ORD record
ord-130e6b76e4c144f3a7794073a6c46351
Source dataset
uspto-grants-1992_02
Patent number
US05086187

Reaction notes

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