Ethyl 3-oxo-3-(pyridin-3-yl)-2-(thiophen-3-yl)propanoate → 1-(Pyridin-3-yl)-2-(thiophen-3-yl)ethanone

HRID 2178072Notes

Reaction equation

[O:1]=[C:2]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:3]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)C(OCC)=O>CS(C)=O.[Cl-].[Na+].O.O>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:2](=[O:1])[CH2:3][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:15]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of ethyl 3-oxo-3-(pyridin-3-yl)-2-(thiophen-3-yl)propanoate (2 g, 7.26 mmol) in DMSO (20 mL) was added catalytic amount of brine (0.2 mL). The reaction mixture was heated at 160° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was concentrated in vacuo and purified by column chromatography to afford Intermediate 56 (1 g, yield 68%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc
concentrationThe organic layer was concentrated in vacuo
custompurified by column chromatography

Sources & evidence

ORD record: ord-a336b39842d94d28b9fb9a17e5dd783e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067893B2

Reaction notes

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