HCID 69892650, compound → HCID 22640052, compound

HRID 2415046Notes

Reaction equation

HRID 2415046 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].[H][H]>CO.[Pd].C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:2]

Participants

6

Reactant 2

HCID 69892650HCID 69892650, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22640052HCID 22640052, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl-2-(3-phenylpropyl)-5-phenyl-2-pentenoate in methanol (10 mL) was added to a suspension of 10% palladium on carbon (0.112 g) in methylene chloride (10 mL) and the mixture was hydrogenated under 60 psi of hydrogen for 6 h. The catalyst was removed by filtration through a pad of celite and the solvent was removed under reduced pressure to give ethyl-2-(3-phenylpropyl)-5-phenyl-pentanoate (0.787 g, 98%). The crude product was not purified further but used directly in the next step. 1H NMR (300 MHz, CDCl3): δ 1.25 (t, 3 H, J=7.1), 1.60 (m, 8 H), 2.39 (m, 1 H), 2.61 (t, 4 H, J=7.3), 4.14 (q, 2 H, J=7.1), 7.24 (m, 10 H).

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8f6ce558e42143b9b2cbc88429b893d9
Source dataset
uspto-grants-2004_11
Patent number
US06818643B1

Reaction notes

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