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

HRID 256555

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-591aa3aa5949400fb4f9a371629c0c57
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258360

Linked notes

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