Pyridine → 3-[2-(5-Acetoxymethyl-2-thienyl)ethenyl]benzo[b]thiophene

HRID 1200053Notes

Reaction equation

HRID 1200053 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([CH:8]=[CH:9][C:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[S:13][CH:14]=2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26]>O>[C:25]([O:1][CH2:2][C:3]1[S:7][C:6]([CH:8]=[CH:9][C:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[S:13][CH:14]=2)=[CH:5][CH:4]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54225068HCID 54225068, compound

Product 1

HCID 542401203-[2-(5-Acetoxymethyl-2-thienyl)ethenyl]benzo[b]thiopheneYield 51.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-[2-(5-hydroxymethyl-2-thienyl)ethenyl]-benzo[b]thiophene (5.35 g) and pyridine (50 ml) was added over 5 mins acetyl chloride (1.54 g). The mixture was stirred at ambient temperature overnight and was poured into water (500 ml). The mixture was extracted with dichlormethane, and the combined organic phase was washed with 5% aqueous hydrochloric acid, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by high performance liquid chromatography (silica gel, sample loaded in dichloromethane, eluted with 15% ethyl acetate in hexane.) The appropriate fractions were combined and concentrated. The residue was recrystallized from cyclohexane to afford 3.15 g (51%) of product, mp 66°-68° C.

Workup

  1. extractionThe mixture was extracted with dichlormethane
  2. washthe combined organic phase was washed with 5% aqueous hydrochloric acid
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by high performance liquid chromatography (silica gel, sample loaded in dichloromethane, eluted with 15% ethyl acetate in hexane.) The appropriate fractions
  7. concentrationconcentrated
  8. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-08892ef21dd746ccb6f8ceb03f86a93e
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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