Ethyl Acetate → HCID 67486387, compound

HRID 1755183Notes

Reaction equation

HRID 1755183 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-7818014670e54dd0a47f11adc3f89011
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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