Tetrahydrofuran → 6-Ethyl-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

HRID 61892Notes

Reaction equation

HRID 61892 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH3:16])([CH3:15])[C:8](=[O:17])[CH2:7][CH2:6]2)#[CH:2].C1COCC1>C(O)C.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH3:16])([CH3:15])[C:8](=[O:17])[CH2:7][CH2:6]2)[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 866638296-Ethynyl-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

Product 1

HCID 668346966-Ethyl-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-oneYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Ethynyl-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (346 mg) was dissolved in ethanol:THF (=2:1 mixture solvent, 20 ml), added with 10% Pd/C (170 mg), and then the mixture was stirred at room temperature for 1 hr under hydrogen atmosphere. The catalyst was removed by filtration and the organic layer was concentrated under reduced pressure to obtain the title compound (322 mg, yield 91%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-067fa3dd93d547be81dfc72aa382c1ac
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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