Ethyl 3-(3-fluorophenyl)-5-methylisoxazole-4-carboxylate → (3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=O)C.C(OC(C1C(C2C=CC=C(F)C=2)=NOC=1C)=O)C>>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:7]2[C:6]([CH2:4][OH:3])=[C:10]([CH3:11])[O:9][N:8]=2)=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 22309060Ethyl 3-(3-fluorophenyl)-5-methylisoxazole-4-carboxylate

HCID 22309061Ethyl 3-(4-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxylate

Product 1

HCID 28473136(3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanolYield 72.4%

Procedure

As described for example 88d, 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (3.0 g, 12 mmol) was converted, instead of 3-(3-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester, to the title compound (1.8 g, 71%) which was obtained as a white solid. MS: m/e=208.1 [M+H]+.

Sources & evidence

ORD record: ord-2fdbfe99f0ff4874ba8f8b4faa92179c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846719B2

Reaction notes

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