Sodium Hydroxide → HCID 86740932, compound

HRID 363981Notes

Reaction equation

HRID 363981 reaction equation
Cl.C(ON)C.[OH-].[Na+].C([C:13]1[C:14](=[O:26])[CH2:15][CH:16]([C:20]2[S:24][C:23]([CH3:25])=[N:22][CH:21]=2)[CH2:17][C:18]=1[OH:19])(=O)CCC>C(O)C.O>[OH:19][C:18]1[CH2:17][CH:16]([C:20]2[S:24][C:23]([CH3:25])=[N:22][CH:21]=2)[CH2:15][C:14](=[O:26])[CH:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178450339HCID 178450339, compound

Product 1

HCID 86740932HCID 86740932, compoundYield 143%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethoxyamine hydrochloride (0.3 g) and then aqueous sodium hydroxide (0.12 g in 1 ml of water) were added to a solution of 2-butyryl-3-hydroxy-5-(2-methyl-5-thiazolyl)cyclohex-2-en-1-one (0.7 g) in ethanol (50 ml) at 20° C. with stirring. After 20 hours, the mixture was diluted with water (200 ml) and then extracted with chloroform (2×100 ml). The dried (MgSO4) organic extract was evaporated to give 2-[1-ethoxyimino)butyl]-3-hydroxy-5-(2-methyl-5-thiazolyl)cyclohex-2-en-1-one (0.75 g, 95%) as a nearly colourless oil which was characterised by proton magnetic resonance spectroscopy (CDCl3 ; δ in ppm); 0.96 (3H, t); 1.31 (3H, t); 1.7 (2H, m); 2.65 (3H, s); 2.5-3.8 (7H, m); 4.10 (2H, q); 7.37 (1H, s); 15.1 (1H, brs).

Workup

  1. extractionextracted with chloroform (2×100 ml)
  2. dry with materialThe dried (MgSO4)
  3. extractionorganic extract
  4. customwas evaporated

Sources & evidence

ORD record
ord-f0946631cc9d413a9909483266e05321
Source dataset
uspto-grants-1986_08
Patent number
US04604132

Reaction notes

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