Ethyl 3-(4-fluorophenyl)hexenoate → Ethyl 3-(4-fluorophenyl)hexanoate

HRID 362877Notes

Reaction equation

HRID 362877 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:15][CH2:16][CH3:17])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H][H]>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:15][CH2:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 54012085Ethyl 3-(4-fluorophenyl)hexenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 23293635Ethyl 3-(4-fluorophenyl)hexanoateYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-(4-fluorophenyl)hexenoate (58.12 g, 0.246 mol) and 10% palladium on carbon (1.1 g, Aldrich) in 95% ethanol was shaken in a Parr hydrogenator under a pressure of 2-4 atm of hydrogen for 0.75 hr. The mixture was filtered and concentrated by spin evaporation in vacuo to give 58.4 g (99.6%) of ethyl 3-(4-fluorophenyl)hexanoate as a clear liquid, NMR (DMSO-d6): d 7.27-7.20 (m, 2H), 7.12-7.04 (m, 2H), 3.91 (q, 2H, J=7.2 Hz), 2.99 (m, 1H), 2.66-2.59 (m, 1H), 2.52-2.44 (m, 1H, partially obscured by DMSO), 1.59-1.46 (m, 2H), 1.13-1.07 (m, 2H), 1.02 (t, 3H, J=7.2Hz), 0.78 (t, 3H, J=7.5 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by spin evaporation in vacuo

Sources & evidence

ORD record
ord-9c92c6400fbf44a8a61f1b4bff857eff
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

Loading…