Potassium Carbonate → HCID 58703306, compound

HRID 501174Notes

Reaction equation

HRID 501174 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17]>CN(C=O)C>[CH:7]([C:5]1[S:6][C:2](/[CH:17]=[CH:16]/[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:3][CH:4]=1)=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15458tert-Butyl acrylateHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 58703306HCID 58703306, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
137.5 °C

Procedure

A mixture of 5-bromothiophene-2-carboxaldehyde (2.41 g, 12.6 mmol), DMF (40 mL), potassium carbonate (1.75 g, 12.6 mmol), tert-butyl acrylate (8 mL, 56.5 mmol), and CombiPhos-Pd6 (200 mg, CombiPhos Catalysts, Inc., P.O. Box 220, Princeton, N.J. 08542) was heated in a 135 to 140° C. oil bath overnight. The solvent was evaporated, the residue stirred in DCM, and the mixture filtered through a pad of diatomaceous earth. The solvent was evaporated and the residue purified by flash chromatography on silica gel eluting with 20% EtOAc/hexane to give an orange solid (1.68 g), m/e=239 (M+1). 1H NMR (CDCl3) ppm: 1.54 (9H, s), 6.36 (1H, d), 7.28 (1H, d), 7.64 (1H, d), 7.68 (1H, d), 9.9 (1H, s).

Workup

  1. customThe solvent was evaporated
  2. filtrationthe mixture filtered through a pad of diatomaceous earth
  3. customThe solvent was evaporated
  4. customthe residue purified by flash chromatography on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-26dbe03647c84aa0b367d6084809eb7b
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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