(+/-)-(E)-1-(4-(2-Phenylethenyl)phenoxy)-4-(3-pyridyl)-2-butanol → HCID 21830747, compound

HRID 1600950Notes

Reaction equation

HRID 1600950 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:26]=[CH:25][C:12]([O:13][CH2:14][CH:15]([OH:24])[CH2:16][CH2:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:1]1([CH2:7][CH2:8][C:9]2[CH:26]=[CH:25][C:12]([O:13][CH2:14][CH:15]([OH:24])[CH2:16][CH2:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 21830666(+/-)-(E)-1-(4-(2-Phenylethenyl)phenoxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 21830747HCID 21830747, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (±)-(E)-1-(4-(2-phenylethenyl)phenoxy)-4-(3-pyridyl)-2-butanol (0.32 g, Example 61) was dissolved in dry ethanol (50 ml) and hydrogenated for 24 hours at 3 atmospheres using palladium on carbon (10%, 0.1 g) as catalyst. The reaction mixture was filtered through Celite® and the residue washed with ethanol. The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:methanol (95:5) to give the title compound as a white solid (0.29 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washthe residue washed with ethanol
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography over silica eluting with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-e4579a396d494de1bd441c88e9e8c030
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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