HCID 58338519, compound → HCID 58338520, compound

HRID 1925453Notes

Reaction equation

HRID 1925453 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:8]=[C:9]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][OH:18])[CH:10]=[CH:11][CH:12]=1>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 58338519HCID 58338519, compound

Product 1

HCID 58338520HCID 58338520, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-[3-(5-Hydroxy-pent-1-ynyl)-phenyl]-pent-4-yn-1-ol (3.40 g, 14.03 mmol) was dissolved in methanol (60 mL) and 10% Pd/C (2.5% w/w) was added. The resulting mixture was hydrogenated on a Parr hydrogenation apparatus (45 psi) for 12 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 (chloroform:methanol 20:1) to afford 3.12 g of the title compound. Yield: 89%. 1H NMR (300 MHz, CDCl3) δ 1.30-1.45 (m, 4H), 1.50-1.72 (m, 8H), 2.59 (t, J=7.8 Hz, 4H), 3.62 (t, J=6.6 Hz, 4H), 6.99 (m, 3H), 7.18 (m, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 25.7, 31.5, 32.8, 36.1, 63.0, 125.8, 128.3, 128.7, 142.5 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 (chloroform:methanol 20:1)

Sources & evidence

ORD record
ord-990428e2c5e045d5934b21fa4331eebc
Source dataset
uspto-grants-2012_05
Patent number
US08178678B2

Reaction notes

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