Acetic Anhydride → 1-tosyl-3-acetylpyrrole

HRID 345950Notes

Reaction equation

HRID 345950 reaction equation
[Cl-].[Ca+2].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-].[C:8](OC(=O)C)(=[O:10])[CH3:9].[S:15]([N:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>ClCCl>[C:8]([C:27]1[CH:28]=[CH:29][N:25]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:22])=[CH:23][CH:24]=2)(=[O:16])=[O:17])[CH:26]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 6400871-TosylpyrroleHCID 5284359Calcium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27377871-tosyl-3-acetylpyrroleYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 1-liter three-neck flask fitted with a thermometer, a 50 cm3 funnel and a condenser with calcium chloride guard, 500 cm3 of dichloromethane and 80 g anhydrous aluminum chloride (600 mmoles) were added. 30 cm3 of acetic anhydride (320 mmoles) was dropwise added. The solution was stirred during 10 minutes. Then a 60 cm3 of dichloromethane solution containing 27 g of 1-tosyl pyrrole 1 (122 mmoles) was dropwise added. The stirring was maintained during 2 hours at room temperature, then the resulting solution was poured on 500 cm3 of water-ice mixture. After decantation, the aqueous layer was extracted with dichloromethane. The combine organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 31 g of purple crystals 2 (M=263, yield: 96.7%). F (° C)=87 (purified by chromatography). NMR: (CDCl3) ppm 7.7 d J(Hz) 8 2H; 7.2 4H; 6.62 2H; 2.35 s 6H.

Workup

  1. additionwere added
  2. additionwas dropwise added
  3. extractionAfter decantation, the aqueous layer was extracted with dichloromethane
  4. washThe combine organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c658b7c853b43afb03430d2ea6bb4ec
Source dataset
uspto-grants-1991_10
Patent number
US05059694

Reaction notes

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