HCID 57733963, compound → HCID 57733960, compound

HRID 469697Notes

Reaction equation

HRID 469697 reaction equation
[C:1]1([C:25]#[C:26][CH2:27][CH2:28][CH2:29][OH:30])[CH:6]=[C:5]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12])[C:4]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:3][C:2]=1[C:19]#[C:20][CH2:21][CH2:22][CH2:23][OH:24]>CO.[Pd]>[C:5]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[C:1]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[C:2]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])=[CH:3][C:4]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]

Participants

4

Reactant 1

HCID 57733963HCID 57733963, compound

Product 1

HCID 57733960HCID 57733960, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5,5′,5″,5′″-(1,2,4,5-benzentetrayl)tetrakis-4-pentyn-1-ol (2.01 g, 4.95 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 psig) 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 (CHCl3:MeOH, 10:1) to afford 1.97 g of the title compound. Yield: 95%. 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, 10:1)

Sources & evidence

ORD record
ord-c25a919458a549889796b1be85833b49
Source dataset
uspto-grants-2014_01
Patent number
US08629163B2

Reaction notes

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