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

HRID 1650396Notes

Reaction equation

HRID 1650396 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-b8863d4272754ec69765a0f25730a8f4
Source dataset
uspto-grants-1990_05
Patent number
US04924002

Reaction notes

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