Pyridine → HCID 14153171, compound

HRID 231453Notes

Reaction equation

HRID 231453 reaction equation
[CH2:1]([S:4][C:5]1[C:9]([Br:10])=[CH:8][S:7][CH:6]=1)[CH:2]=[CH2:3].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Br:10][C:9]1[C:5]2[S:4][CH2:1][CH2:2][CH2:3][C:6]=2[S:7][CH:8]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 14153170HCID 14153170, compound

Product 1

HCID 14153171HCID 14153171, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 30.2 g (0.13 mol) of 3-allylthio-4-bromothiophene and 10.3 mls (0.13 mol) of pyridine in 250 mls of toluene was refluxed for 68 hours, cooled, washed with 1N HCl solution, 1N NaOH solution, water and brine and dried over MgSO4 and concentrated to give 27.2 g of an amber oil. The oil was chromatographed on 500 g of SiO2 eluting with hexane to give 16.2 g of the desired product as a colorless oil (90% purity).

Workup

  1. temperaturecooled
  2. washwashed with 1N HCl solution, 1N NaOH solution, water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9ae3186b5233469588b5f166ed9cc779
Source dataset
uspto-grants-1989_07
Patent number
US04846874

Reaction notes

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