Methyl Thioglycolate → Methyl 1,3-dioxa-5-thia-s-indacene-6-carboxylate

HRID 335552

Reaction equation

[CH2:1]1[O:5][C:4]2[CH:6]=[C:7](Br)[C:8]([CH:10]=O)=[CH:9][C:3]=2[O:2]1.[H-].[Na+].[SH:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>>[O:2]1[C:3]2[CH:9]=[C:8]3[CH:10]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[S:15][C:7]3=[CH:6][C:4]=2[O:5][CH2:1]1

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 950621,3-Benzodioxole-5-carboxaldehyde, 6-bromo-

Product 1

HCID 11746624Methyl 1,3-dioxa-5-thia-s-indacene-6-carboxylate

Procedure

Using 3.0 g (13.1 mmol) of 6-bromopiperonal, 0.79 g (19.7 mmol) of sodium hydride (60% pure) and 1.53 g (14.4 mmol) of methyl mercaptoacetate, 732 mg (18.5% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-4699895698a54beeb68d51851ddc4bd2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884017B2

Linked notes

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