Potassium Carbonate → tert-butyl (2E)-3-(3-formyl-2-thienyl)acrylate

HRID 64430Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]=[O:8].[C:9]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH:10]=[CH2:11].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:7]([C:6]1[CH:5]=[CH:4][S:3][C:2]=1/[CH:11]=[CH:10]/[C:9]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:8]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 1 g of 2-bromothiophene-3-carbaldehyde, 3.8 ml of tert-butyl acrylate, 120 mg of palladium acetate, 420 mg of tetra-n-butylammonium bromide, and 610 mg of potassium carbonate in 10 ml of DMF was stirred at 100° C. overnight. After leaving to be cooled, the insoluble material was filtered through Celite, and to the filtrate were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 660 mg of tert-butyl (2E)-3-(3-formyl-2-thienyl)acrylate.

Workup

customAfter leaving
temperatureto be cooled
filtrationthe insoluble material was filtered through Celite
additionto the filtrate were added water and ethyl acetate
customa layer separation operation
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ed9ee36aef7240c194eee930d48cb9d9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447090B2

Reaction notes

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