Methyl 3-methyl-1-benzofuran-6-carboxylate → Methyl 3-methyl-2,3-dihydrobenzofuran-6-carboxylate

HRID 2170487Notes

Reaction equation

HRID 2170487 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:5]=2[O:4][CH:3]=1.[H][H]>[Pd].CO>[CH3:1][CH:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 2

HCID 22481752Methyl 3-methyl-1-benzofuran-6-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 89580905Methyl 3-methyl-2,3-dihydrobenzofuran-6-carboxylateYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-methylbenzofuran-6-carboxylate (400 mg, 2.1 mmol), palladium on carbon (50 mg, 0.56 mmol), in methanol (10 mL) was charged with hydrogen (0.4 MPa) at room temperature for 12 hours. Then filtered, and the organic layer was concentrated to dryness and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give the product methyl 3-methyl-2,3-dihydrobenzofuran-6-carboxylate (384 mg, 95%) as white solid. LRMS (M+H+) m/z: calcd 192.21. found 192. 1H NMR (300 MHz, CDCl3) δ 7.54-7.51 (m, 1H), 7.27-7.22 (m, 2H), 4.72-4.66 (m, 1H), 4.10-4.06 (m, 1H), 3.56-3.53 (m, 1H), 1.32 (m, 3H).

Workup

  1. filtrationThen filtered
  2. concentrationthe organic layer was concentrated to dryness
  3. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-46226ae7b6ad4e24bba9d323ce030052
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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