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Triethylamine → Ethyl 3-(5-formyl-1-benzofuran-3-yl)prop-2-enoate

HRID 2261096
Notes
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Reaction equation

HRID 2261096 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 574696633-Bromo-benzofuran-5-carbaldehyde

Product 1

HCID 71378267Ethyl 3-(5-formyl-1-benzofuran-3-yl)prop-2-enoateYield 42%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

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

  1. customThe tube was sealed
  2. filtrationThe crude was filtered on celite
  3. customThe solvents were evaporated
  4. customthe crude was purified by silicagel chromatography
  5. customA pale yellow solid was obtained (400 mg, yield:42%)

Sources & evidence

ORD record
ord-f4d802f03c984fe0bd3cdb2b634c75fe
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846925B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes