5-Methyl-3-m-tolyl-isoxazole-4-carboxylic acid ethyl ester → (5-Methyl-3-(p-tolyl)isoxazol-4-yl)methanol

Reaction equation

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

Participants

Reactant 2

HCID 223090555-Methyl-3-m-tolyl-isoxazole-4-carboxylic acid ethyl ester

HCID 22309056Ethyl 5-methyl-3-(P-tolyl)isoxazole-4-carboxylate

Product 1

HCID 28473118(5-Methyl-3-(p-tolyl)isoxazol-4-yl)methanolYield 38%

Procedure

As described for example 249d, 5-methyl-3-p-tolyl-isoxazole-4-carboxylic acid ethyl ester (12.6 g, 51.4 mmol) was converted, instead of 5-methyl-3-m-tolyl-isoxazole-4-carboxylic acid ethyl ester, to the title compound (3.95 g, 38%) which was obtained as a white solid. MS: m/e=204.2 [M+H]+.

Sources & evidence

ORD record: ord-59b9afb679d2464b8ce486cb71f647bc
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518974B2

Reaction notes

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