Pyridine → HCID 14153171, compound

HRID 648863Notes

Reaction equation

HRID 648863 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-a58f4a6fc25b4729a34c417d77126df9
Source dataset
uspto-grants-1988_04
Patent number
US04737184

Reaction notes

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