Water → HCID 18989186, compound

HRID 2395547Notes

Reaction equation

HRID 2395547 reaction equation
[CH:1]1([C:4](=[O:25])[C:5](=[CH:21]OCC)[C:6]([C:8]2[CH:18]=[CH:17][C:11]3[S:12][CH:13]=[C:14]([O:15][CH3:16])[C:10]=3[C:9]=2[O:19][CH3:20])=[O:7])[CH2:3][CH2:2]1.Cl.[NH2:27]O.C([O-])(=O)C.[Na+].O>C(O)C>[CH:1]1([C:4]2[O:25][N:27]=[CH:21][C:5]=2[C:6]([C:8]2[CH:18]=[CH:17][C:11]3[S:12][CH:13]=[C:14]([O:15][CH3:16])[C:10]=3[C:9]=2[O:19][CH3:20])=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 53989599HCID 53989599, compound

Product 1

HCID 18989186HCID 18989186, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution containing 5-(3-cyclopropyl-2-ethoxymethylene-1,3-dioxoprop-1-yl)-3,4-dimethoxybenzo[b]thiophene (0.59 g) and hydroxylamine hydrochloride (0.137 g) was stirred for 15 minutes in ethanol. Sodium acetate (anhydrous, 0.161 g) was added and the mixture stirred for 4 hours, before evaporation of the ethanol and addition of water. The mixture was extracted with ethyl acetate, dried (anhydrous magnesium sulphate) and evaporated in vacuo. The residue was purified by column chromatography on silica, eluting with ether/cyclohexane to yield 5-cyclopropyl-4-(3,4dimethoxybenzo[b]thien-5-oyl)isoxazole (compound 3, 0.24 g) as an oil, NMR δ1.20 (2H,m), 1.35 (2H,m), 2.80 (1H,m), 3.84 (3H,s), 4.00 (3H,s), 6.39 (1H,s), 7.40 (1H, d), 7.59 (1H, d), 8.29 (1H,s).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried (anhydrous magnesium sulphate)
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica
  5. washeluting with ether/cyclohexane

Sources & evidence

ORD record
ord-658ebb7edb284616869f87852ba6206c
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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