Water → HCID 18953279, compound

HRID 1491556Notes

Reaction equation

HRID 1491556 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[CH:12]=[C:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]=[CH:9][C:8]=1[C:18](=[O:29])[C:19](=[CH:25]OCC)[C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21].Cl.[NH2:31]O.O>C(O)C>[Cl:6][C:7]1[CH:12]=[C:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]=[CH:9][C:8]=1[C:18]([C:19]1[CH:25]=[N:31][O:21][C:20]=1[CH:22]1[CH2:24][CH2:23]1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 53795986HCID 53795986, compound

Product 1

HCID 18953279HCID 18953279, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (1.52 g) was added to a stirred mixture of 1-[2-chloro-4-(methylsulphonyloxy)phenyl]-3-cyclopropyl-2-ethoxymethylenepropan-1,3-dione (5.6 g) and hydroxylamine hydrochloride (1.3 g) in ethanol. The mixture was stirred for 0.75 hours. Water was added and the mixture was extracted with dichloromethane. The organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of ethyl acetate and dichloromethane to give 4-[2-chloro-4-(methylsulphonyloxy)benzoyl]-5-cyclopropylisoxazole (compound 1, 4.60 g) as a brown oil, NMR (CDCl3) 1.25-1.35(m,2H), 1,4-1.5 (m,2H), 2.6-2.7(m, 1H), 3.2(s, 1H), 7.3(d, 1H), 7.4(s, 1H), 7.45 (d, 1H), 8.15 (s, 1H).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography
  7. washeluted with a mixture of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-87eba126154a4c70908684273d511dc5
Source dataset
uspto-grants-1994_12
Patent number
US05371063

Reaction notes

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