HCID 20823138, compound → HCID 20823153, compound

HRID 585200Notes

Reaction equation

HRID 585200 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][CH:15]=[CH2:16])[CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[C:5]([CH3:24])([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][CH2:15][CH3:16])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 20823138HCID 20823138, compound

Product 1

HCID 20823153HCID 20823153, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(3-allyl-4-hydroxyphenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester (330 mg, 0.97 mmol) in absolute EtOH (5 mL) was treated with 5% Pd/C and then the mixture was evacuated three times with N2. The reaction mixture was hydrogenated at 1 atm with an H2-filled balloon for 24 h before filtering the mixture over celite and rinsing with EtOH. The product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.22 (t, J=7.6 Hz, 2H), 7.99-6.95 (m, 3H), 6.82 (m, 2H), 6.68 (d, J=8.0 Hz, 1H), 4.20 (q, J=6.8 Hz, 2H), 3.24 (A of AB, J=13.6 Hz, 1H), 3.08 (B of AB, J=13.6 Hz, 1H), 2.55 (t, J=7.6 Hz, 2H), 1.62 (sextet, J=7.6 Hz, 2H), 1.41 (s, 3H), 1.23 (t, J=6.8 Hz, 3H), 0.96 (t, J=7.2 Hz, 3H).

Workup

  1. customthe mixture was evacuated three times with N2
  2. additionfilled balloon for 24 h
  3. filtrationbefore filtering the mixture over celite
  4. washrinsing with EtOH
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-edd6577aa07541ecb0928f41f90d07b4
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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