4-Toluenesulfonyl chloride → 1-Tosylpyrrole

HRID 1844741Notes

Reaction equation

HRID 1844741 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li]CCCC.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>C1COCC1>[S:11]([N:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8027PyrroleHCID 178418339Butyllithium

Product 1

HCID 6400871-TosylpyrroleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1H-pyrrole (5.0 g, 74.6 mmol) in dry THF (50 mL) was added n-BuLi (32.8 mL, 2.5 M) at −78° C. and stirred at this temperature for 30 min. Then a solution of TsCl (14.2 g, 74.6 mmol) in dry THF (100 mL) was added at −78° C. The mixture was stirred at rt overnight, quenched with water and extracted with EA twice. The combined organic layers were washed with brine and concentrated to give crude compound 27a (14.2 g, 86%) as a solid.

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. customquenched with water
  3. extractionextracted with EA twice
  4. washThe combined organic layers were washed with brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-51f264a5ce004f26b92a3f5f7e4c098e
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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