Tetrahydrofuran → HCID 86689406, compound

HRID 926665Notes

Reaction equation

HRID 926665 reaction equation
I[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][C:3]=1[O:11][CH3:12].[C:13]([CH:15]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])#[CH:14].O1[CH2:34][CH2:33][CH2:32][CH2:31]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C(N(CC)CC)C>[CH2:16]([CH:15]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:13]#[C:14][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([C:31]#[C:32][CH:33]([CH2:34][CH2:17][CH2:16][CH2:15][CH2:13][CH3:14])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])=[CH:4][C:3]=1[O:11][CH3:12])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 6391731,4-diiodo-2,5-dimethoxybenzeneHCID 86689405HCID 86689405, compound

Product 1

HCID 86689406HCID 86689406, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

1,4-Diiodo-2,5-dimethoxy-benzene (3.750 g; 9.616 mmol), 7-ethynyl-pentadecane (4.2) (5.116 g; 21.637 mmol), PdCl2(PPh3)2 (0.169 g; 240 μmol) and copper iodide (0.092 g; 481 μmol) are dissolved into tetrahydrofuran (50 cm3) and triethylamine (50 cm3). The resulting mixture is degassed for 30 minutes and then stirred at 60° C. for 17 hours. The solvent is removed in vacuo and the crude product purified by column chromatography (gradient from 100:00 to 75:25, Petroleum ether (40-60° C.) and dichlorobenzene) to afford a light yellow oil which crystallises upon standing (4.90 g, Yield: 84%). NMR (1H, 300 MHz, CDCl3): δ 6.83 (s, 2H); 3.81 (s, 6H); 2.59 (m, 2H); 1.53 (m, 16H); 1.31 (m, 32H); (m, 12H).

Workup

  1. customThe resulting mixture is degassed for 30 minutes
  2. customThe solvent is removed in vacuo
  3. customthe crude product purified by column chromatography (gradient from 100:00 to 75:25, Petroleum ether (40-60° C.) and dichlorobenzene)
  4. customto afford a light yellow oil which
  5. customcrystallises

Sources & evidence

ORD record
ord-90beedaed52742b3b8329ed0e9438c80
Source dataset
uspto-grants-2016_03
Patent number
US09287504B2

Reaction notes

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