Chloroacetone → 2-Thiophenecarboxylic acid, 5-acetyl-4-hydroxy-, methyl ester

Reaction equation

Cl[CH2:2][C:3](=[O:5])[CH3:4].[C:6]([C:12]([O:14][CH3:15])=[O:13])#[C:7][C:8](OC)=[O:9].[SH-:16].[Na+]>>[C:3]([C:2]1[S:16][C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:8]=1[OH:9])(=[O:5])[CH3:4]

Participants

Reactant 3

HCID 6571Chloroacetone

HCID 12980Dimethyl acetylenedicarboxylate

HCID 28015Sodium hydrosulfide

Product 1

HCID 106080802-Thiophenecarboxylic acid, 5-acetyl-4-hydroxy-, methyl ester

Procedure

According to the description in Synth. Commun., 1996, 26, 1083, methyl 2-acetyl-3-hydroxythiophene-5-carboxylate was synthesized with chloroacetone, dimethyl acetylene dicarboxylate and sodium hydrosulfide as starting materials (yield: 60%).

Sources & evidence

ORD record: ord-ecc73145941641afa70ccfc6f141ecaa
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291449B2

Reaction notes

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