Methyl acetoacetate → Methyl (4-carboxy-3-thienyl)acetate

HRID 1460913Notes

Reaction equation

Br[C:2]1[C:3]([C:7]([OH:9])=[O:8])=[CH:4][S:5][CH:6]=1.[C:10]([O:16][CH3:17])(=[O:15])[CH2:11]C(C)=O>>[C:7]([C:3]1[C:2]([CH2:11][C:10]([O:16][CH3:17])=[O:15])=[CH:6][S:5][CH:4]=1)([OH:9])=[O:8]

Participants

Reactant 2

HCID 7757Methyl acetoacetate

HCID 855464-Bromo-3-thenoic acid

Product 1

HCID 14326173Methyl (4-carboxy-3-thienyl)acetate

Procedure

Methyl (4-carboxy-3-thienyl)acetate was prepared from 4-bromothiophen-3-carboxylic acid and methyl acetoacetate by the method described by D. E. Ames and O. Ribeiro, J. Chem. Soc., Perkin I., 1975, 1390, for the preparation of the corresponding ethyl ester. It is a solid which, after crystallisation from aqueous methanol, had mp 121°-122° C., 1H nmr: delta 3.72 (3H, s), 3.95 (2H, s), 7.18 (1H, d J 3 Hz), 8.27 (1H, d J 3 Hz) ppm.

Workup

customafter crystallisation from aqueous methanol

Sources & evidence

ORD record: ord-85cc2d56d49b46dea2f9f9700444fbc3
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05073184

Reaction notes

Loading…