(Z)-Benzaldehyde oxime → 5-(1-Hydroxypropyl)-3-phenylisoxazole

HRID 1613868Notes

Reaction equation

HRID 1613868 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]#[C:11][CH:12]([OH:15])[CH2:13][CH3:14].Cl[O-].[Na+]>ClCCl>[OH:15][CH:12]([C:11]1[O:9][N:8]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 12143(Z)-Benzaldehyde oximeHCID 929811-Pentyn-3-olHCID 23665760Sodium Hypochlorite

Product 1

HCID 151807655-(1-Hydroxypropyl)-3-phenylisoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 12.5 ml of dichloromethane, were dissolved 2.5 g (20.7 mmol) of benzaldoxime and 2.1 g (25.0 mmol) of 1-pentyne-3-ol. Under ice cooling, 14.5 g of a 12.0% aqueous solution of sodium hypochlorite were added dropwise to the solution. After completion of the dropwise addition, they were reacted at room temperature for 3 hours, followed by the extraction of the organic layer with dichloromethane. The extract was washed with water and the resulting organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by chromatography on a silica gel column (eluent: chloroform), whereby the target compound, namely, 5-(1-hyroxypropyl)-3-phenylisooxazole was obtained as crystals.

Workup

  1. additionAfter completion of the dropwise addition, they
  2. customwere reacted at room temperature for 3 hours
  3. extractionfollowed by the extraction of the organic layer with dichloromethane
  4. washThe extract was washed with water
  5. dry with materialthe resulting organic layer was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by chromatography on a silica gel column (eluent: chloroform), whereby the target compound

Sources & evidence

ORD record
ord-5d84d9a410634b26b58a722d6575a435
Source dataset
uspto-grants-1993_03
Patent number
US05194606

Reaction notes

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