Sodium Hydroxide → HCID 136209532, compound

HRID 542662Notes

Reaction equation

HRID 542662 reaction equation
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].[OH-].[Na+].[OH:8][C:9]1[CH2:14][CH:13]([C:15]2[C:16]([O:25][CH3:26])=[N:17][C:18]([O:23][CH3:24])=[N:19][C:20]=2[O:21][CH3:22])[CH2:12][C:11](=[O:27])[C:10]=1[C:28](=O)[CH2:29][CH3:30]>C(O)C.O>[CH2:2]([O:4][N:5]=[C:28]([C:10]1[C:9](=[O:8])[CH2:14][CH:13]([C:15]2[C:16]([O:25][CH3:26])=[N:17][C:18]([O:23][CH3:24])=[N:19][C:20]=2[O:21][CH3:22])[CH2:12][C:11]=1[OH:27])[CH2:29][CH3:30])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178458886HCID 178458886, compound

Product 1

HCID 136209532HCID 136209532, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethoxyamine hydrochloride (0.30 g) and then aqueous sodium hydroxide (0.15 g in 2 ml of water) were added to a solution of 3-hydroxy-5-(2,4,6-trimethoxy-5-pyrimidyl)-2-propionylcyclohex-2-en-1-one (0.90 g) in absolute ethanol (30 ml) at 20° C. with stirring. After 20 hours at 20° C. the mixture was diluted with water (150 ml) and extracted with chloroform (2×75 ml). The chloroform layer was dried over anhydrous magnesium sulphate and the solvent was removed by evaporation under reduced pressure to give 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethoxy-5-pyrimidyl)cyclohex-2-en-1-one (900 mg) as a pale yellow oil. The product was characterized by nuclear magnetic resonance spectroscopy.

Workup

  1. extractionextracted with chloroform (2×75 ml)
  2. dry with materialThe chloroform layer was dried over anhydrous magnesium sulphate
  3. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-09fcce7d22654a3ea72dfaa1af909cba
Source dataset
uspto-grants-1987_04
Patent number
US04659362

Reaction notes

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