2,3-dimethoxy-5-[(E)-2-phenylethenyl]pyridine → 2,3-Dimethoxy-5-(2-phenylethyl)pyridine

HRID 709021Notes

Reaction equation

HRID 709021 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][N:4]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 867315242,3-dimethoxy-5-[(E)-2-phenylethenyl]pyridine2×

Product 1

HCID 711858192,3-Dimethoxy-5-(2-phenylethyl)pyridineYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask containing a solution of 2,3-dimethoxy-5-[(E)-2-phenylethenyl]pyridine (Intermediate 5) (0.07 g, 0.29 mmol) in ethanol (10 ml) was evacuated and flushed with nitrogen. Palladium (10% on carbon) (0.03 g, 0.03 mmol) was added and the reaction vessel was evacuated and flushed with nitrogen before being filled with hydrogen gas from a balloon and stirred at room temperature for 45 minutes. The catalyst was removed by filtration through a pad of celite which was then washed with ethanol (20 ml). The combined organics were concentrated in vacuo to give 2,3-dimethoxy-5-(2-phenylethyl)pyridine as a colourless oil (70 mg, 99%).

Workup

  1. customwas evacuated
  2. customflushed with nitrogen
  3. customthe reaction vessel was evacuated
  4. customflushed with nitrogen
  5. additionbefore being filled with hydrogen gas from a balloon
  6. customThe catalyst was removed by filtration through a pad of celite which
  7. washwas then washed with ethanol (20 ml)
  8. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-1f7bb3019a0e4c68b5b1f2148df0ecca
Source dataset
uspto-grants-2015_11
Patent number
US09180122B2

Reaction notes

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