Ethanol → HCID 69823809, compound

HRID 342789Notes

Reaction equation

HRID 342789 reaction equation
C(OC1C=CC=C(OCC[CH:14]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:15][O:16][C:17]2[CH:25]=[CH:24]C3CCOC=3[C:18]=2[CH2:26][CH:27]([CH3:29])[CH3:28])C=1)(=O)C.[ClH:36].NO.[C:39]([O-:42])(=[O:41])[CH3:40].[Na+].[CH2:44]([OH:46])[CH3:45]>>[Cl:36][C:45]1[CH:32]=[C:31]([CH2:40][C:39]([OH:42])=[O:41])[CH:30]=[CH:35][C:44]=1[O:46][CH2:26][CH2:18][CH:17]([O:16][C:15]1[CH:14]=[CH:24][C:25]2[CH:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:15][O:16][C:17]=2[C:18]=1[CH2:26][CH:27]([CH3:28])[CH3:29])[CH3:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86753574HCID 86753574, compound

Product 1

HCID 69823809HCID 69823809, compound

Procedure

A mixture of Methyl-3-Chloro-4(3-(3-phenyl-7-isobutyl-(2H-benzofuran-6-yloxy)butyloxy)-phenyl acetate (328 mg, 0.58 mmoles), hydroxylamine hydrochloride (202 mg, 2.9 mmoles), anhydrous sodium acetate (238 mg, 2.9 mmoles) and ethanol (4 ml) was heated under reflux in a nitrogen atmosphere with magnetic stirring for 2 hr. The mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted twice with ethyl acetate. The combined ethyl acetate phases were washed with water, 10% NaHCO3 solution, and saturated NaCl solution, and dried (MgSO4). Evaporation in vacuo and purification by chromatography (silica gel, 4:1 hexane-ethyl acetate) gave the title compound as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a nitrogen atmosphere
  3. customThe mixture was partitioned between ethyl acetate and water
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washThe combined ethyl acetate phases were washed with water, 10% NaHCO3 solution, and saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. customEvaporation
  8. customin vacuo and purification by chromatography (silica gel, 4:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-df3890ef3aa94a9d84e41e89cf38cc99
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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