HCID 59323507, compound → HCID 59323506, compound

HRID 1749003Notes

Reaction equation

HRID 1749003 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[C:11]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][OH:18])[CH:10]=[C:9]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:8]=1>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[CH:10]=[C:9]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:8]=1

Participants

4

Reactant 1

HCID 59323507HCID 59323507, compound

Product 1

HCID 59323506HCID 59323506, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1,3,5-tris-(5-hydroxy-1-pentynyl)benzene (2.84 g, 8.6 mmol) was dissolved in methanol (30 mL) and 10% Pd/C (5% w/w) was added. The resulting mixture was hydrogenated on a Parr hydrogenation apparatus (45 psi) for 4 hours. 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 (CHCl3:MeOH 6:1) to afford 2.84 g of 1,3,5-tris-(5-hydroxypentyl)benzene. Yield 96%. 1H NMR (300 MHz, CDCl3) δ 6.81 (s, 3H), 3.62 (t, J=6.3 Hz, 6H), 2.57 (t, J=7.5 Hz, 6H), 1.53-1.70 (m, 12H), 1.38 (m, 6H) ppm; 13C NMR (75 MHz, CDCl3) δ 142.5, 126.1, 63.1, 36.1, 32.9, 31.5, 25.7 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 (CHCl3:MeOH 6:1)

Sources & evidence

ORD record
ord-44aaca36d9474145b480a78382c5f544
Source dataset
uspto-grants-2015_10
Patent number
US09155733B2

Reaction notes

Loading…