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

HRID 331836Notes

Reaction equation

HRID 331836 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl: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>>[Cl: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

3

Reactant 2

HCID 22309060Ethyl 3-(3-fluorophenyl)-5-methylisoxazole-4-carboxylateHCID 66643827Ethyl 3-(4-chlorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 15121509(3-(4-Chlorophenyl)-5-methylisoxazol-4-yl)methanolYield 65.2%

Procedure

As described for example 88d, 3-(4-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (373 mg, 1.4 mmol) was converted, instead of 3-(3-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester, to the title compound (204 mg, 65%) which was obtained as a white solid. MS: m/e=224.1 [M+H]+.

Sources & evidence

ORD record
ord-d8cdd1a7a8c54bbda12bca17c46b56a7
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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