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 253199Notes

Reaction equation

HRID 253199 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]>CCO.[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 88.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (195 mg) was added to a suspension of 6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl ester (1.07 g, 4.32 mmol) and FeCl3, (5 mg) in EtOH (30 mL) under N2. The suspension was hydrogenated at 40 psi for 3 days. The suspension was filtered through a Celite pad and the filtrate was concentrated to a leave crude oil. The oil was purified using medium pressure chromatography on silica (CHCl3) to provide a colorless oil (886 mg, 88.3% yield). 1H-NMR (300 MHz, CDCl3) δ 1.28 (t, J=7.2 Hz, 3H). 1.84 (m, 1H), 2.19 (m, 1H), 2.70 (m, 1H), 2.83 (m, 2H), 2.93 (m, 2H), 3.77 (s, 3H), 4.17 (q, J=7.2 Hz, 2H), 6.62 (s, 1H), 6.69 (dd, J=8.4, 2.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe suspension was filtered through a Celite pad
  2. concentrationthe filtrate was concentrated to
  3. customa leave crude oil
  4. customThe oil was purified

Sources & evidence

ORD record
ord-616cf7b8e1d042529243fa45226975c7
Source dataset
uspto-grants-2011_01
Patent number
US07872023B2

Reaction notes

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