(E)-3-(4-Benzyloxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-acrylic Acid Ethyl Ester → 3-(4-Hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-propionic Acid Ethyl Ester

HRID 1726988Notes

Reaction equation

HRID 1726988 reaction equation
[CH2:1]([O:3][C:4](=[O:25])/[CH:5]=[CH:6]/[C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([O:17]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([OH:17])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 69035743(E)-3-(4-Benzyloxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-acrylic Acid Ethyl Ester

Product 1

HCID 585664753-(4-Hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-propionic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.15 g (3.41 mmol) of the above prepared (E)-3-(4-benzyloxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-acrylic acid ethyl ester was dissolved in 20 ml of tetrahydrofuran and hydrogenated over 0.3 g of 10% of palladium on charcoal as catalyst at ambient temperature and atmospheric pressure. Filtering off the catalyst and evaporating the solvent yielded 0.84 g of the title compound as grey solid.

Workup

  1. filtrationFiltering off the catalyst
  2. customevaporating the solvent

Sources & evidence

ORD record
ord-2d872f6d990741db974a8eab93086a14
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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