HCID 66993584, compound → HCID 59678331, compound

HRID 251609Notes

Reaction equation

HRID 251609 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([C:19]([CH2:23][CH2:24][CH3:25])=[CH:20][CH2:21][CH3:22])=[CH:13][N:12]=1)[CH3:2]>CO.[Pd]>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([CH:19]([CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH3:25])=[CH:13][N:12]=1)[CH3:10]

Participants

4

Reactant 1

HCID 66993584HCID 66993584, compound

Product 1

HCID 59678331HCID 59678331, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(2,6-diethyl-phenyl)-4-methoxy-5 (1-propyl-but-1-enyl)-pyridine (20 mg) and 10% Pd/C (20 mg) in MeOH (1 mL) is hydrogenated at 50 psi overnight. The mixture is filtered through celite and washed with MeOH. The filtrate is concentrated to give 2-(2,6-diethyl-phenyl)-4-methoxy-5-(1-propyl-butyl)-pyridine. 1H NMR (CDCl3) 8.29 (s, 1H), 7.26 (d, 1H), 7.13 (d, 2H), 6.71 (s, 1H), 3.81 (s, 3H), 3.00 (m, 1H), 2.37 (m, 4H), 1.65 (m, 4H), 1.23 (m, 4H), 1.07 (t, 6H), 0.86 (t, 6H).

Workup

  1. customis hydrogenated at 50 psi overnight
  2. filtrationThe mixture is filtered through celite
  3. washwashed with MeOH
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-614f9e78ea074beeadb907e9542bade2
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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