5-(1,1'-Biphenyl-4-yl)-4-pentyn-1-ol → [1,1'-Biphenyl]-4-pentanol

HRID 84346Notes

Reaction equation

HRID 84346 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 230493185-(1,1'-Biphenyl-4-yl)-4-pentyn-1-ol

Product 1

HCID 10657698[1,1'-Biphenyl]-4-pentanolYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(1,1′-biphenyl-4-yl)-4-pentyn-1-ol (3.89 g, 16.46 mmol) was dissolved in methanol (30 mL), and 10% Pd/C (2.5% w/w) was added. The resulting mixture was hydrogenated on a Parr hydrogenation apparatus (45 psi) for 4 hrs. The catalyst was removed by filtration through a Celite pad. The filter cake was rinsed with methanol, and the combined organic liquors were concentrated under reduced pressure. The crude product was purified by column chromatography (hexanes:ethyl acetate 1:1) to afford 3.48 g of the title compound. Yield: 88%. 1H NMR (300 MHz, CDCl3) δ 1.35-1.48 (m, 3H), 1.55-1.74 (m, 4H), 2.66 (t, J=7.5 Hz, 2H), 3.64 (t, J=6.6 Hz, 2H), 7.21-7.60 (m, 9H) ppm; 13C NMR (75 MHz, CDCl3) δ 25.7, 31.5, 32.9, 35.8, 63.1, 127.08, 127.13, 128.8, 128.9, 138.7, 141.2, 141.8 ppm.

Workup

  1. customThe catalyst was removed by filtration through a Celite pad
  2. washThe filter cake was rinsed with methanol
  3. concentrationthe combined organic liquors were concentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (hexanes:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-21100f0059c54dce895d9089e5745722
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Reaction notes

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