Ethyl Acetate → Ethyl 3-phenylisoxazole-5-carboxylate

HRID 58556Notes

Reaction equation

HRID 58556 reaction equation
[CH:1]1C=CC(C2C=CC(NC3C=CC=CC=3)=CC=2)=CC=1.[OH:20]/[N:21]=[C:22](/Cl)\[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+].[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36]>O>[C:23]1([C:22]2[CH:1]=[C:36]([C:35]([O:38][CH2:39][CH3:40])=[O:37])[O:20][N:21]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 5875529(E)-N-Hydroxybenzimidoyl chlorideHCID 13087229N-phenyl-(1,1'-biphenyl)-4-amine

Product 1

HCID 4201981Ethyl 3-phenylisoxazole-5-carboxylateYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl propriolate (0.657 mL; 6.43 mmol), (E)-N-hydroxybenzimidoyl chloride (0.500 g; 3.21 mmol) and sodium bicarbonate (0.818 g; 9.64 mmol) in a mixture of ethyl acetate (16 mL) and water (1 mL) was stirred at room temperature. overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 5 to 80% dichloromethane in heptane) to furnish 0.295 g (42%) of ethyl 3-phenylisoxazole-5-carboxylate.

Workup

  1. customovernight
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica gel (eluent 5 to 80% dichloromethane in heptane)

Sources & evidence

ORD record
ord-277c9b648abf4dca94876a28b66a120d
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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