6-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl ester → 6-Methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester

HRID 278460Notes

Reaction equation

HRID 278460 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[C:7]1=O)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 110757986-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl ester

Product 1

HCID 110965286-Methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl esterYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(RS)-6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (2.0 g, 8.05 mmol) in MeOH (20 ml) and Pd/C (10%), (200 mg) was stirred vigorously under a hydrogen atmosphere for 3 hr at ambient temperature. The catalyst was removed and solvent evaporated to afford an oil, which was purified by chromatography over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (1:9) to afford (RS)-6-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester as a colourless oil (1.88 g, 6.14 mmol, 76%), MS ml/e=234.1 (M+).

Workup

  1. customThe catalyst was removed
  2. customsolvent evaporated
  3. customto afford an oil, which
  4. customwas purified by chromatography over SiO2 (Merck 230-400 mesh)
  5. washeluting with EtOAc-nHexane (1:9)

Sources & evidence

ORD record
ord-ec069ef2474a443eb7f54f7b628c8b7d
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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