HCID 66870587, compound → HCID 66870819, compound

HRID 1691583Notes

Reaction equation

HRID 1691583 reaction equation
[C:1]([C:7]1[C:15]2[S:16][CH:17]=[CH:18][C:14]=2[C:13]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:9]2[S:10][CH:11]=[CH:12][C:8]=12)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]>C1COCC1.[Pd]>[CH2:1]([C:7]1[C:15]2[S:16][CH:17]=[CH:18][C:14]=2[C:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:9]2[S:10][CH:11]=[CH:12][C:8]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 66870587HCID 66870587, compound

Product 1

HCID 66870819HCID 66870819, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above prepared 4,8-dihexynylbenzo[1,2-b:4,5-b′]dithiophene (3 grams, 8.6 mmol) in THF (150 milliliters) in a round-bottomed flask was added 10 percent Pd/C (0.90 gram, 0.86 mmol). The mixture was stirred under a hydrogen atmosphere at room temperature for 24 hours. The solvent was removed by vacuum evaporation, and the residue with the catalyst impurity was purified by column chromatography on silica gel (eluent: hexane/dichloromethane, 2/1, v/v). Recrystallization of the product isolated from column chromatography from 20 milliliters of isopropanol in fridge afforded 1.54 grams (51 percent yield) of needle crystal after drying in vacuo.

Workup

  1. customThe solvent was removed by vacuum evaporation
  2. customthe residue with the catalyst impurity was purified by column chromatography on silica gel (eluent
  3. customRecrystallization of the product
  4. customisolated from column chromatography from 20 milliliters of isopropanol in fridge

Sources & evidence

ORD record
ord-8e228573f47c4ae48bc866a0f3652b9a
Source dataset
uspto-grants-2012_04
Patent number
US08153755B2

Reaction notes

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