HCID 58401217, compound → HCID 58261094, compound

HRID 868776Notes

Reaction equation

HRID 868776 reaction equation
[CH2:1]([CH:3]([CH2:27][CH2:28][CH2:29][CH3:30])[C:4]#[C:5][C:6]1[C:14]2[S:13][CH:12]=[CH:11][C:10]=2[C:9]([C:15]#[C:16][CH:17]([CH2:22][CH3:23])[CH2:18][CH2:19][CH2:20][CH3:21])=[C:8]2[S:24][CH:25]=[CH:26][C:7]=12)[CH3:2]>[Pd].C1COCC1>[CH2:22]([CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][CH2:15][C:9]1[C:8]2[S:24][CH:25]=[CH:26][C:7]=2[C:6]([CH2:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:27][CH2:28][CH2:29][CH3:30])=[C:14]2[S:13][CH:12]=[CH:11][C:10]=12)[CH3:23]

Participants

4

Reactant 1

HCID 58401217HCID 58401217, compound

Product 1

HCID 58261094HCID 58261094, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A dry 250 mL 1-neck flask was flushed with N2 and was charged with 4,8-bis(3-ethylhept-1-ynyl)thieno[2,3-f]benzothiophene (3.04 g, 0.007 mol), Pd/C wet support (0.82 g, 10%) and THF (15 mL, 0.5 M). The flask was evacuated and backfilled with hydrogen. The flask was kept under a hydrogen atmosphere and was monitored by TLC. After the reaction was completed, the mixture was filtered through Celite and solvent was removed by rotary evaporation. The solid was dissolved in hexanes and purified by column chromatography to yield oil (1.66 g, 54%).

Workup

  1. customA dry 250 mL 1-neck flask was flushed with N2
  2. customThe flask was evacuated
  3. filtrationthe mixture was filtered through Celite and solvent
  4. customwas removed by rotary evaporation
  5. dissolutionThe solid was dissolved in hexanes
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-9d6dedd5906e404490d11b8f63788366
Source dataset
uspto-grants-2015_03
Patent number
US08968885B2

Reaction notes

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