HCID 14739696, compound → HCID 54372303, compound

HRID 1110086Notes

Reaction equation

HRID 1110086 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH:20]=[CH2:21])[CH:13]=2)[CH:6]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH2:20][CH3:21])[CH:13]=2)[CH:6]=1)[CH3:2]

Participants

4

Reactant 1

HCID 14739696HCID 14739696, compound

Product 1

HCID 54372303HCID 54372303, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(3-allyl-4-hydroxyphenoxy)benzoic acid ethyl ester (Gapinski, D. M.; Mallet, B. E.; Froelich, L. L.; Jackson, W. T., J. Med. Chem., 33, 2798-2813 (1990) incorporated herein by reference; 2.45 g) in methanol (15 mL) was added 10% palladium-on-carbon (300 mg). Hydrogen was bubbled through the resulting suspension for 5 minutes. The mixture was placed under 1 arm of hydrogen with stirring for 48 hours at room temperature. The mixture was de-gassed with nitrogen, filtered, and concentrated in vacuo to give 2.38 g (96%) of the title product as a colorless oil: 1H-NMR (CDCl3) 7.74 (d, J=8 Hz, 1H), 7.64 (d, J=2 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 7.15 (dd, J=9, 2 Hz, 1H), 6.86 (dd, J=2 Hz, 1H), 6.78 (m, 2H), 5.14 (bs, 1H, --OH), 4.38 (q, J=7 Hz, 2H), 2.59 (t, J=7 Hz, 2H), 1.65 (hextet, J=8 Hz, 2H), 1.39 (t, J=7 Hz, 3H), 0.98 (t, J=7 Hz, 3H).

Workup

  1. customHydrogen was bubbled through the resulting suspension for 5 minutes
  2. customThe mixture was de-gassed with nitrogen
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d68164fc431494dac143d3693889f2b
Source dataset
uspto-grants-1994_06
Patent number
US05324743

Reaction notes

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