Methyl 4-ethynyl-3-hydroxybenzoate → Methyl 6-benzofurancarboxylate

HRID 408567Notes

Reaction equation

HRID 408567 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[CH:13])[C:5]([O:7][CH3:8])=[O:6]>C1(C)C=CC=CC=1>[O:1]1[C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]=2[CH:12]=[CH:13]1

Participants

3

Reactant 1

HCID 86702025Methyl 4-ethynyl-3-hydroxybenzoate

Product 1

HCID 22481705Methyl 6-benzofurancarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-hydroxy-4-ethynylbenzoate (1 eq.) in dry toluene was added PtCl2 (0.1 eq.) under argon. The reaction mixture was stirred at 80° C. for 1.5 h, warmed to 20° C. and the solvents removed under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 9/1) to afford methyl benzofuran-6-carboxylate.

Workup

  1. temperaturewarmed to 20° C.
  2. customthe solvents removed under reduced pressure
  3. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 9/1)

Sources & evidence

ORD record
ord-c9eb168d6fe1476c8eccc162875c299d
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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