Triethylamine → Ethyl 3-(5-formyl-1-benzofuran-3-yl)prop-2-enoate
Reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.[CH2:39]([O:41][C:42](=[O:45])[CH:43]=[CH2:44])[CH3:40]>C(#N)C>[CH2:39]([O:41][C:42](=[O:45])[CH:43]=[CH:44][C:2]1[C:6]2[CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1)[CH3:40]Participants
6
Conditions
- Temperature
- 120 °C
Procedure
In a sealed tube 3-Bromo-1-benzofuran-5-carbaldehyde (500 mg, 2.22 mmol) was dissolved in 7 ml of ACN. To this solution was added PPh3 (1.16 g, 4.44 mmol), Pd(II)acetate (500 mg, 2.2 mmol), Et3N (073 mL, 5.55 mmol) and finally acrylic acid ethyl ester (2.41 ml, 22 mmol). The tube was sealed and the reaction was heated at 120° C. for one hour. The crude was filtered on celite to eliminate inorganic contaminations. The solvents were evaporated and the crude was purified by silicagel chromatography using cyclohexane-AcOEt 95-5 to 50-50. A pale yellow solid was obtained (400 mg, yield:42%).
Workup
- customThe tube was sealed
- filtrationThe crude was filtered on celite
- customThe solvents were evaporated
- customthe crude was purified by silicagel chromatography
- customA pale yellow solid was obtained (400 mg, yield:42%)
Sources & evidence
- ORD record
- ord-f4d802f03c984fe0bd3cdb2b634c75fe
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846925B2
Reaction notes
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