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

HRID 1479747Notes

Reaction equation

HRID 1479747 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-4761673455b24af9987e153a5c16e9b2
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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