HCID 69353500, compound → 2-Phenoxy-3-(naphthalen-1-yl)-2-methylpropionic acid ethyl ester

HRID 348297Notes

Reaction equation

HRID 348297 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](OCC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:33])[C:5]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 69353500HCID 69353500, compound

Product 1

HCID 693540102-Phenoxy-3-(naphthalen-1-yl)-2-methylpropionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Phenoxy-3-(4-benzyloxynaphthalen-1-yl)-2-methylpropionic acid ethyl ester (1.55 g, 3.5 mmol) was dissolved in ethyl acetate (50 mL) and treated with 5% palladium on carbon (400 mg), and stirred under an atmosphere of hydrogen for 20 h. The suspension was filtered through celite and concentrated in vacuo to a golden oil (1.20 g, 98%) 1H NMR (300 MHz, CDCl3): δ 8.14 (d, 1H, J=8.3), 8.10 (d, 1H, J=8.3), 7.46 (t, 1H, J=8.3), 7.42 (t, 1H, J=8.3), 7.21 (d, 1H, J=7.8), 7.12 (dd, 2H, J=8.8, 7.4), 6.87 (t, 1H, J=7.4), 6.70 (m, 3H), 4.05 (q, 2H, J=6.8), 3.65 (d, 1H, J=14.2), 3.54 (d, 1H, J=14.2), 1.37 (s, 3H), 1.17 (t, 3H, J=6.8). MS [EI+] 373 (M+Na)+, [EI−] 349 (M−H).

Workup

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated in vacuo to a golden oil (1.20 g, 98%) 1H NMR (300 MHz, CDCl3): δ 8.14 (d, 1H, J=8.3), 8.10 (d, 1H, J=8.3), 7.46 (t, 1H, J=8.3), 7.42 (t, 1H, J=8.3), 7.21 (d, 1H, J=7.8), 7.12 (dd, 2H, J=8.8, 7.4), 6.87 (t, 1H, J=7.4), 6.70 (m, 3H), 4.05 (q, 2H, J=6.8), 3.65 (d, 1H, J=14.2), 3.54 (d, 1H, J=14.2), 1.37 (s, 3H), 1.17 (t, 3H, J=6.8)

Sources & evidence

ORD record
ord-6a7f3bd60be54e9b9d7d75dae3c0d15a
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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