Methanol → Methyl 6-methoxybenzofuran-3-carboxylate

HRID 1865213Notes

Reaction equation

HRID 1865213 reaction equation
FC(F)(F)S(O[C:7]1[C:11]2[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:10]=2[O:9][CH:8]=1)(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:49][OH:50].C(N(CC)CC)C.CN(C)[CH:60]=[O:61]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:11]2[C:7]([C:49]([O:61][CH3:60])=[O:50])=[CH:8][O:9][C:10]=2[CH:15]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 77230216Trifluoro-methanesulfonic acid 6-methoxy-benzofuran-3-yl ester

Product 1

HCID 53419774Methyl 6-methoxybenzofuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

6-Methoxybenzofuran-3-yl trifluoromethane sulfonate (500 mg, 1.69 mmol) was added to a stainless steel high-pressure reaction vessel then dissolved in N,N-dimethylformamide (6.5 mL). Carbon monoxide gas was bubbled through the solution for 10 minutes. 1,3-Bis(diphenylphosphino)propane (21 mg, 0.051 mmol), methanol (1.8 mL), triethylamine (342 mg, 3.38 mmol) and palladium acetate (11 mg, 0.051 mmol) were added to the reaction mixture, while continuing to bubble carbon monoxide gas through the mixture. The reaction vessel was sealed and charged with carbon monoxide (30 psi). The reaction mixture was heated at 80 C for 4.5 hours. The mixture was concentrated in vacuo. The remaining orange mixture was purified by silica gel chromatography (5% ethyl acetate/hexane) to afford methyl 6-methoxybenzofuran-3-carboxylate as a light yellow solid. MS (ESI, pos. ion) m/z: 207.1 (M+1).

Workup

  1. customCarbon monoxide gas was bubbled through the solution for 10 minutes
  2. customto bubble carbon monoxide gas through the mixture
  3. customThe reaction vessel was sealed
  4. additioncharged with carbon monoxide (30 psi)
  5. temperatureThe reaction mixture was heated at 80 C for 4.5 hours
  6. concentrationThe mixture was concentrated in vacuo
  7. customThe remaining orange mixture was purified by silica gel chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d2346b9810e04d06aed58164b3ef4f24
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

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