2-Benzofurancarboxaldehyde → HCID 11805206, compound

HRID 377362Notes

Reaction equation

HRID 377362 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.[CH:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13]>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:14]/[CH:12]=[O:13]

Participants

4

Reactant 2

HCID 613412-BenzofurancarboxaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde2×

Product 1

HCID 11805206HCID 11805206, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzofuran-2-carboxaldehyde (2.2 g, 15.1 mmol) and formylmethylenetriphenylphosphorane (4.6 g, 15.1 mmoles) in CH2Cl2 (150 mL) was refluxed for 6 hours. Another aliquot of formylmethylenetriphenylphosphorane (1.5 g, 4.93 mmol) was then added and the reflux continued overnight. The reaction mixture was cooled to RT, the solvent concentrated at reduced pressure and the residue was chromatographed on silicagel (n-heptane/EtOAc 4/1). The collected fractions were pooled and concentrated and the residue triturated with isopropyl ether to give, after drying, pure title compound (1.3 g, 7.55 mmol, yield 50.0%) as pale yellow crystals, m.p.=67°.

Workup

  1. concentrationthe solvent concentrated at reduced pressure
  2. customthe residue was chromatographed on silicagel (n-heptane/EtOAc 4/1)
  3. concentrationconcentrated
  4. customthe residue triturated with isopropyl ether
  5. customto give
  6. customafter drying

Sources & evidence

ORD record
ord-f184e02592cc4d94a145a15fc5d7df16
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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