Ethyl 3-(naphthalen-1-yl)prop-2-enoate → Ethyl 3-(1-naphthyl)propanoate

HRID 381791Notes

Reaction equation

HRID 381791 reaction equation
[C:1]1([CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>CCO.[Pd]>[C:1]1([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 53428571Ethyl 3-(naphthalen-1-yl)prop-2-enoate

Product 1

HCID 10966256Ethyl 3-(1-naphthyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7 (12 g, 53.1 mmol) in 95% EtOH (180 mL) was hydrogenated over 10% Pd.C (600 mg) at room temperature using an H2 filled balloon (overnight). The reaction mixture was filtered and taken to dryness to give a 8 as a clear oil80 (11.9 g, 98%). 1H NMR (CDCl3) δ 8.05 (1H, d, J=7.8 Hz), 7.86 (1H, dd, J=2.7, 7.6 Hz), 7.75 (1H, d, J=7.6 Hz), 7.35˜7.58 (4H, m), 4.17 (2H, q, J=7.1 Hz), 3.44 (2H, t, J=8.1 Hz), 2.77 (2H, t, J=8.3 Hz), 1.26 93H, t, J=7.1 Hz).

Workup

  1. customat room temperature
  2. customan H2 filled balloon (overnight)
  3. filtrationThe reaction mixture was filtered
  4. customto give a 8 as a clear oil80 (11.9 g, 98%)

Sources & evidence

ORD record
ord-caf5da090a1a4379806e2fd748fc4b37
Source dataset
uspto-grants-2001_10
Patent number
US06307090B1

Reaction notes

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