HCID 13978687, compound → HCID 58338527, compound

HRID 1925451Notes

Reaction equation

HRID 1925451 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]#[C:14][CH2:15][CH2:16][CH2:17][OH:18]>C(O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]

Participants

4

Reactant 1

HCID 13978687HCID 13978687, compound

Product 1

HCID 58338527HCID 58338527, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-[2-(5-Hydroxy-pent-1-ynyl)-phenyl]-pent-4-yn-1-ol (2.70 g, 11.14 mmol) was dissolved in ethanol (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 (chloroform:methanol 20:1) to afford 2.55 g of the title compound. Yield: 91%. 1H NMR (300 MHz, CDCl3) δ 1.38-1.67 (m, 12H), 2.60 (t, J=7.8 Hz, 4H), 3.59 (t, J=6.6 Hz, 4H), 7.11 (m, 4H) ppm; 13C NMR (75 MHz, CDCl3) δ 26.0, 31.3, 32.6, 32.8, 62.6, 125.8, 129.1, 140.2 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-ffd8799be8e74ee3b1a8e98e3a3067b3
Source dataset
uspto-grants-2012_05
Patent number
US08178678B2

Reaction notes

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