HCID 86689406, compound → HCID 68028053, compound

HRID 926666Notes

Reaction equation

HRID 926666 reaction equation
[CH2:1]([CH:7]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:8]#[C:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([C:18]#[C:19][CH:20]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][C:11]=1[O:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>O1CCCC1.[Pd]>[CH2:1]([CH:7]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([CH2:18][CH2:19][CH:20]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][C:11]=1[O:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 86689406HCID 86689406, compound

Product 1

HCID 68028053HCID 68028053, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

1,4-Bis-(3-hexyl-undec-1-ynyl)-2,5-dimethoxy-benzene (4.3) (7.70 g, 12.1 mmol) is dissolved in tetrahydrofuran (200 cm3) under an atmosphere of Argon. 10% Pd/C (1.25 g) is added, the mixture warmed to 30° C. (oil bath temperature) and stirred under an atmosphere of hydrogen for 2.5 hours. The reaction mixture is filtered through a plug of celite and the plug washed through with ethyl acetate (2×50 cm3), and the filtrate is concentrated in vacuo. The crude oil is purified by column chromatography eluting with 2 to 5% ethyl acetate in petroleum ether (40-60° C.). A second purification by column chromatography is carried out, eluting with 3% ethyl acetate in petroleum ether (40-60° C.) to give the title product as a colourless oil (7.00 g, 90%). NMR (1H, 400 MHz, CDCl3): δ 6.65 (s, 2H); 3.78 (s, 6H); 2.53 (m, 4H); 1.51 (m, 4H); 1.28 (m, 50H); 0.89 (m, 12H)

Workup

  1. filtrationThe reaction mixture is filtered through a plug of celite
  2. washthe plug washed through with ethyl acetate (2×50 cm3)
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe crude oil is purified by column chromatography
  5. washeluting with 2 to 5% ethyl acetate in petroleum ether (40-60° C.)
  6. customA second purification by column chromatography
  7. washeluting with 3% ethyl acetate in petroleum ether (40-60° C.)

Sources & evidence

ORD record
ord-21bc9006cbeb4dad8760809e5f09f0f4
Source dataset
uspto-grants-2016_03
Patent number
US09287504B2

Reaction notes

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