Benzaldehyde → Isoxazole, 5-methyl-3-phenyl-

HRID 2352644Notes

Reaction equation

HRID 2352644 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1C(=O)[CH2:14][CH2:13][C:12]1=O.C(OC(C)=C)(=O)C.C(N(CC)CC)C.C(=O)C1C=CC=CC=1>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[C:2]1([C:1]2[CH:12]=[C:13]([CH3:14])[O:9][N:8]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 7916Isopropenyl acetateHCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide

Product 1

HCID 136803Isoxazole, 5-methyl-3-phenyl-Yield 45.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
4 °C

Procedure

Benzaldehyde oxime (20.0 g, 0.165 mole) is dissolved in DMF (250 mL) and cooled to 4° C. in an ice bath. N-chlorosuccinimide (33.1 g, 0.248 mole) is added to the reaction mixture, and the mixture is stirred for one hour. Isopropenyl acetate (41.3 g, 0.41 mole) and triethyl amine (24.8 g, 0.247 mole) are added via an equal-pressure addition funnel to the solution of benzaldehyde hydroxamic chloride. The ice bath is removed and the mixture is stirred for 24 hours. The mixture is then taken up into ethyl acetate (1 L) and washed with water (2×1 L). The organic layer is dried over sodium sulfate and evaporated to give a residue. Flash chromatography (hexane/ethyl acetate 9:1) affords 12.0 g of 3-phenyl-5-methylisoxazole as a yellow oil.

Workup

  1. customThe ice bath is removed
  2. stirringthe mixture is stirred for 24 hours
  3. washwashed with water (2×1 L)
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customevaporated
  6. customto give a residue

Sources & evidence

ORD record
ord-80639ebae2ab4779b34f8da33c270041
Source dataset
uspto-grants-1989_10
Patent number
US04877881

Reaction notes

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