Methyl 6-benzofurancarboxylate → Methyl 2,3-dihydro-1-benzofuran-6-carboxylate

HRID 869866Notes

Reaction equation

HRID 869866 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1>CO.[Pd]>[O:1]1[C:5]2[CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 22481705Methyl 6-benzofurancarboxylate

Product 1

HCID 59942373Methyl 2,3-dihydro-1-benzofuran-6-carboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl benzofuran-6-carboxylate (17.8 g, 100 mmol) and 10% Pd/C (10.5 g) in MeOH was stirred under hydrogen atmosphere at 50 psi for 2 h. The catalyst was removed by filtration. The solvent was removed under reduced pressure to afford the desired methyl 2,3-dihydrobenzofuran-6-carboxylate (17.8 g, 98.5% yield). 1H NMR (400 MHz, CDCl3) δ: 7.57 (d, J=7.6, 1H), 7.40 (s, 1H), 7.23 (d, J=7.6, 1H), 4.61 (t, J=8.8, 2H), 3.89 (s, 3H), 3.25 (t, J=8.8, 2H).

Workup

  1. customThe catalyst was removed by filtration
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c399ff16d6024c4282a6d42966a22ac5
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

Loading…