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

HRID 434045Notes

Reaction equation

HRID 434045 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4](=[N:6][OH:7])Cl.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[C:14]#[C:15][CH3:16].C(N(CC)CC)C>C(OCC)C>[CH2:19]([O:18][C:13]([C:14]1[C:4]([C:3]2[CH:8]=[CH:9][C:10]([F:12])=[CH:11][C:2]=2[F:1])=[N:6][O:7][C:15]=1[CH3:16])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78043Ethyl 2-butynoateHCID 72739620HCID 72739620, compound

Product 1

HCID 18756262Ethyl 3-(2,4-difluorophenyl)-5-methylisoxazole-4-carboxylateYield 58.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a fashion similar to that for preparation 15, 2,4-difluorobenzoyl chloride oxime (2.00 g, 10.4 mmol), ethyl 2-butynoate (1.76 g, 15.7 mmol), triethyl amine (2.9 ml, 21 mmol) in diethyl ether (10 ml), and diethyl ether 30 ml) gave 4-ethoxycarbonyl-5-methyl-3-(2,4-difluorophenyl)isoxazole (1.62 g, 58%) after column chromatography (silica gel, hexanes/diethyl ether gradient).

Sources & evidence

ORD record
ord-697a748a35cd46fea06243f62f2a72dc
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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