Ethyl Acrylate → 3-(Benzofuran-6-yl)-acrylic acid ethyl ester

HRID 322077

Reaction equation

HRID 322077 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(=O)C.[Na+]>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:16]([O:15][C:11](=[O:14])[CH:12]=[CH:13][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[CH:3]=1)[CH3:17]

Participants

8

Reactant 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 517045Sodium AcetateHCID 151587226-Bromo-1-benzofuran

Product 1

HCID 539711413-(Benzofuran-6-yl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the 6-bromo-benzofuran 3-3 (1.74 g, 8.79 mmol), ethyl acrylate (1.09 g, 10.98 mmol), Pd(OAc)2 (0.099 g, 0.44 mmol), tri-o-tolylphosphine (0.268 g, 0.880 mmol), and sodium acetate (3.60 g, 43.9 mmol) in DMF (10 mL) was heated to 100° C. in a sealed tube for 4 h. The mixture was cooled to room temperature, diluted with water, and extracted with Et2O (2×40 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate/hexanes) to give the ester 3-4 as an off-white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with Et2O (2×40 mL)
  3. washThe combined organic extracts were washed with brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-14359deede9c42e59a42fe459b57b871
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Linked notes

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