Acetic Anhydride → HCID 20458181, compound

HRID 544728Notes

Reaction equation

HRID 544728 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)[C:5]([CH3:13])=[CH:4][C:3]=1[CH:14]([CH3:17])[CH:15]=[CH2:16].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:9]=[CH:10][CH:11]=[CH:12]2)[C:5]([CH3:13])=[CH:4][C:3]=1[CH:14]([CH3:17])[CH:15]=[CH2:16])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20458191HCID 20458191, compound

Product 1

HCID 20458181HCID 20458181, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A few drops of pyridine are added to a solution of 26.7 g (0.12 mole) of 3-[2-hydroxy-5-methyl-4-(pyrrol-1-yl)-phenyl]-1-butene in 370 ml of acetic anhydride and the mixture is stirred at room temperature for 2 hours. The reaction mixture is poured onto ice and extracted three times with methylene chloride. The methylene chloride phases are washed with dilute sodium bicarbonate solution, then with water, until neutral, are combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. Filtration over a little silica gel with methylene chloride yields 3-[2-acetoxy-5-methyl-4-(pyrrol-1-yl)-phenyl]-1-butene, Rf (toluene/ethyl acetate=10:1): 0.55.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted three times with methylene chloride
  3. washThe methylene chloride phases are washed with dilute sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in a vacuum rotary evaporator
  6. filtrationFiltration over a little silica gel with methylene chloride

Sources & evidence

ORD record
ord-80e73ddec4064a3e926abda6fab3799d
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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