HCID 68874238, compound → HCID 14979359, compound

HRID 2224826Notes

Reaction equation

HRID 2224826 reaction equation
C([O:8][C:9](=[O:21])[C:10]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][CH:12]=[CH2:13])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH3:20][C:10]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([CH2:11][CH2:12][CH3:13])[C:9]([OH:21])=[O:8]

Participants

4

Reactant 1

HCID 68874238HCID 68874238, compound

Product 1

HCID 14979359HCID 14979359, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-2-phenyl-pent-4-enoic acid benzyl ester (2.31 g, 8.24 mmol) in ethyl acetate (20 mL) was treated with 10% palladium on carbon (0.24 g, 10 weight percent) and stirred under a hydrogen balloon for 72 hours. The vessel was purged with nitrogen gas and the mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to give the title compound (1.58 g, 99%). 1H NMR (300 MHz, CDCl3): δ ppm 0.91 (m, 3 H) 1.23 (m, 2 H) 1.57 (m, 3 H) 1.96 (m, 2 H) 7.36 (m, 5 H). MS (DCI/NH3+) m/z 210 (M+NH4)30.

Workup

  1. customThe vessel was purged with nitrogen gas
  2. filtrationthe mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2c66a16168854da78209552d2445513c
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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