(Z)-Benzaldehyde oxime → Methyl 3-phenylisoxazole-4-carboxylate

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.C(=NO)C1C=CC=CC=1>>[C:5]1([C:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][O:10][N:9]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 12143(Z)-Benzaldehyde oxime

HCID 870083HCID 870083, compound

Product 1

HCID 10750662Methyl 3-phenylisoxazole-4-carboxylateYield 35%

Procedure

This compound was synthesised following the procedure described for Compound 8C but using benzaldoxime instead of 4-fluorobenzaldoxime as a starting material. The crude was purified twice by flash chromatography (toluene-acetone 96:4 followed by toluene) to give the title compound as an oil (35%).

Workup

customThis compound was synthesised
customThe crude was purified twice by flash chromatography (toluene-acetone 96:4 followed by toluene)

Sources & evidence

ORD record: ord-cfdb9f3188974a09821b1fe5d45b71e2
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365591B1

Reaction notes

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