Methyl Thioglycolate → 6-Methoxy-benzo[B]thiophene-2-carboxylic acid methyl ester

HRID 658167Notes

Reaction equation

F[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[H-].[Na+].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[S:14][C:2]=2[CH:9]=1

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 27348732-Fluoro-4-methoxybenzaldehyde

Product 1

HCID 534861116-Methoxy-benzo[B]thiophene-2-carboxylic acid methyl ester

Procedure

Using 2.5 g (16.2 mmol) of 2-fluoro-4-methoxybenzaldehyde, 0.97 g (24.3 mmol) of sodium hydride (60% pure) and 1.89 g (17.8 mmol) of methyl mercaptoacetate, 3.05 g (84.7% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-3affe92ddbaa4321a214bbe9ae83ec58
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076355B2

Reaction notes

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