ethyl 2-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)acetate → Ethyl 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate

HRID 1909522Notes

Reaction equation

HRID 1909522 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8][CH2:7][CH2:6]2.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 67405611ethyl 2-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 13420659Ethyl 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetateYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the alkene (512) (0.792 g, 3.22 mmol) in ethanol (53 mL) was added Pd/C (100 mg, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred under a hydrogen balloon overnight at room temperature, then filtered through a pad of celite and concentrated in vacuo to give ethyl 2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate (513) (0.708 g, 88.7%) as a colorless oil.

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with hydrogen three times
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57f2ba0a2b854a50a12a1f16acadfcfb
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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