Sodium Hydroxide → HCID 135999353, compound

HRID 1583883Notes

Reaction equation

HRID 1583883 reaction equation
[OH-].[Na+].Cl.[CH2:4]([O:6][NH2:7])[CH3:5].[OH:8][C:9]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[CH2:12][C:11](=[O:23])[C:10]=1[C:24](=O)[CH2:25][CH3:26]>O.C(O)C>[CH2:4]([O:6][N:7]=[C:24]([C:10]1[C:11](=[O:23])[CH2:12][CH:13]([C:15]2[CH:16]=[CH:17][C:18]([S:21][CH3:22])=[CH:19][CH:20]=2)[CH2:14][C:9]=1[OH:8])[CH2:25][CH3:26])[CH3:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178458883HCID 178458883, compound

Product 1

HCID 135999353HCID 135999353, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (0.15 g) in water (5 ml) and then ethoxyamine hydrochloride (0.37 g) were added to a solution of 3-hydroxy-5-(4-methylthiophenyl)-2-propionylcyclohex-2-en-1-one (1.0 g) in ethanol (40 ml). The mixture was stirred at room temperature and the progress of the reaction was monitored by thin layer chromatography on silica gel (eluant dichloromethane). On completion of the reaction the solvent was removed by distillation under reduced pressure. The residue was treated with dichloromethane and the organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to give 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(4-methylthiophenyl)cyclohex-2-en-1-one (0.95 g) as a yellow oil.

Workup

  1. customOn completion of the reaction the solvent
  2. customwas removed by distillation under reduced pressure
  3. additionThe residue was treated with dichloromethane
  4. washthe organic phase was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-75c23a165c664f2b94a348ec44c019b8
Source dataset
uspto-grants-1985_11
Patent number
US04555263

Reaction notes

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