HCID 21830680, compound → HCID 21830678, compound

HRID 1600942Notes

Reaction equation

HRID 1600942 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[C:17][CH:18]([OH:27])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]([OH:27])[CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 21830680HCID 21830680, compound

Product 1

HCID 21830678HCID 21830678, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(3'-acetylbiphenyl-4-yl)-5-(3-pyridyl)pent- 1-yn-3-ol (0.7 g) in absolute ethanol (20 ml) was hydrogenated for 24 hours at 1.2 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 combined filtrate and washings were concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:methanol (97:3) to give the title compound as a colourless oil (0.25 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washthe residue washed with ethanol
  3. concentrationThe combined filtrate and washings were concentrated under reduced pressure
  4. customThe residue was purified by column chromatography over silica eluting with dichloromethane:methanol (97:3)

Sources & evidence

ORD record
ord-2cffc15acaf444a5a4f80eab67cc3821
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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