Ethyl Acetate → HCID 67486387, compound

HRID 2371288Notes

Reaction equation

HRID 2371288 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:26]([O:28]CC2C=CC=CC=2)=[O:27])[C:12]2[CH:17]=[CH:16][C:15]([O:18]CC3C=CC=CC=3)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.CCOC(C)=O>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:26]([OH:28])=[O:27])[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 67486405HCID 67486405, compound

Product 1

HCID 67486387HCID 67486387, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-[2-benzyloxycarbonyl-2-(4-benzyloxy-phenyl)-ethyl]-benzoic acid methyl ester (Step C, 3.0 g, 6.66 mmol) in EtOH:EtOAc (50 mL, 1:1 ratio) at rt, was added 10% palladium on carbon (0.3 g), hydrogenated at 1 atm. H2 (gas) and the reaction mixture was stirred at rt for 14 h. The reaction mixture was filtered through celite plug and washed with ethyl acetate (50 mL) and concentrated under reduced pressure. The crude product was dried under vacuum for 3 h to afford 4-[2-carboxy-2-(4-hydroxy-phenyl)-ethyl]-benzoic acid methyl ester as a white solid (1.6 g, 86%): 1H NMR (300 MHz, CDCl3): δ 7.83 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 7.08 (dd, J=4.62, 12.5 Hz, 2H), 6.66 (dd, J=6.6, 12.5 Hz, 2H), 3.79 (s, 3H), 3.75 (t, J=8.1 Hz, 1H), 3.22 (dd, J=8.4, 13.5 Hz, 1H), 2.93 (dd, J=7.2, 13.8 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through celite plug
  2. washwashed with ethyl acetate (50 mL)
  3. concentrationconcentrated under reduced pressure
  4. dry with materialThe crude product was dried under vacuum for 3 h

Sources & evidence

ORD record
ord-43641103eb504cd78b07796109d54c6d
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

Loading…