Diethyl Malonate → 3-(4-Carboxybutyl)-5-methylisoxazole

Reaction equation

[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][CH2:8][CH2:9]Br)[CH:3]=1.C(OCC)(=O)[CH2:12][C:13]([O:15]CC)=[O:14].CC1ON=C(CCC(O)=O)C=1>>[C:13]([CH2:12][CH2:9][CH2:8][CH2:7][C:4]1[CH:3]=[C:2]([CH3:1])[O:6][N:5]=1)([OH:15])=[O:14]

Participants

Reactant 3

HCID 7761Diethyl Malonate

HCID 1333605-Methyl-3-isoxazolepropionic acid

HCID 133169753-(3-Bromopropyl)-5-methyl-1,2-oxazole

Product 1

HCID 133169763-(4-Carboxybutyl)-5-methylisoxazoleYield 56%

Procedure

3-(4-Carboxybutyl)-5-methylisoxazole was prepared from 5-methyl-3-(3-bromopropyl)isoxazole and diethyl malonate according to the procedure of part (c) above, and was obtained in 56% yield as a colorless solid, m.p. 58°-60° C. when recrystallized from carbon tetrachloride.