Triethylamine → Methyl 3-(2,6-difluorophenyl)-5-methylisoxazole-4-carboxylate

HRID 434038Notes

Reaction equation

HRID 434038 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:4](=[N:6][OH:7])Cl.[CH3:13][O:14][C:15](=[O:19])[C:16]#[C:17][CH3:18].C(N(CC)CC)C>C(OCC)C>[CH3:13][O:14][C:15]([C:16]1[C:4]([C:3]2[C:2]([F:1])=[CH:11][CH:10]=[CH:9][C:8]=2[F:12])=[N:6][O:7][C:17]=1[CH3:18])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 141019Methyl but-2-ynoateHCID 533953822,6-Difluorobenzoyl chloride oxime

Product 1

HCID 18756257Methyl 3-(2,6-difluorophenyl)-5-methylisoxazole-4-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a fashion similar to that for preparation 15, 2,6-difluorobenzoylchloride oxime (1.00 g, 5.19 mmol), methyl-2-butynoate (1.01 g, 10.4 mmol), triethyl amine (0.94 ml, 6.8 mmol) in diethyl ether (3 ml), and diethyl ether (25 ml) afforded 4-methoxycarbonyl-5-methyl-3-(2,6-difluorophenyl)isoxazole (0.80 g, 61%) after purification by column chromatography (silica gel, hexanes/diethyl ether gradient).

Sources & evidence

ORD record
ord-6026291be8084c51b7e0479860c9a254
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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