Hydroxylamine, O-ethyl- → HCID 178449937, compound

HRID 462379Notes

Reaction equation

[C:1]([CH:6]1[C:11](=[O:12])[CH:10]([CH3:13])[CH:9]([CH2:14][CH:15]([S:17][CH2:18][CH3:19])[CH3:16])[CH2:8][C:7]1=[O:20])(=O)[CH2:2][CH2:3][CH3:4].[CH2:21]([O:23][NH2:24])[CH3:22]>C(O)C>[CH2:21]([O:23][NH:24][C:1](=[C:6]1[C:11](=[O:12])[CH:10]([CH3:13])[CH:9]([CH2:14][CH:15]([S:17][CH2:18][CH3:19])[CH3:16])[CH2:8][C:7]1=[O:20])[CH2:2][CH2:3][CH3:4])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

Into 10 ml of ethanol, 2.97 g of 2-butyryl-5-(2-ethylthiopropyl)-4-methylcyclohexane-1,3-dione was dissolved and 0.81 g of ethoxyamine was dropped thereto at 0° C. and the resulting solution was stirred at room temperature for 3 hours. After pouring the reaction solution into ice-cold water, the mixture was extracted with chloroform. The chloroform solution was washed with water and extracted with 1N-sodium hydroxide solution. The sodium hydroxide solution was acidified with 1N-hydrochloric acid and the acidified mixture was extracted with chloroform. The chloroform solution was washed with water and dried over anhydrous magnesium sulfate. The removal of chloroform by distillation under reduced pressure gave 3.0 g of the desired product as yellow oily material. Yield 88%, nD19.5 1.5375.

Workup

additionAfter pouring the reaction solution into ice-cold water
extractionthe mixture was extracted with chloroform
washThe chloroform solution was washed with water
extractionextracted with 1N-sodium hydroxide solution
extractionthe acidified mixture was extracted with chloroform
washThe chloroform solution was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe removal of chloroform
distillationby distillation under reduced pressure

Sources & evidence

ORD record: ord-11d7f2702e6544a48977873e50b25cfe
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04515729

Reaction notes

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