Pyridine → Methyl 4-acetoxy-3-(pyrrol-1-yl)benzoate

HRID 399836Notes

Reaction equation

HRID 399836 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.N1C=CC=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[C:23]([O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1)(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 18945287Methyl 4-hydroxy-3-(pyrrol-1-yl)benzoate

Product 1

HCID 18945175Methyl 4-acetoxy-3-(pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 4-hydroxy-3-(pyrrol-1-yl)benzoate (15.0 g), pyridine (8.4 ml) and acetic anhydride (9.8 ml) in dichloromethane (75 ml) was stirred for 15 hours at ambient temperature. To the reaction mixture was added the mixture of dichloromethane and water and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate solution. The separated organic layer was washed with 1N-hydrochloric acid and water respectively. The organic layer was dried over magnesium sulfate and evaporated in vacuo to give methyl 4-acetoxy-3-(pyrrol-1-yl)benzoate (15.9 g).

Workup

  1. additionTo the reaction mixture was added
  2. washThe separated organic layer was washed with 1N-hydrochloric acid and water respectively
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-cc6f1f0948e14bcbaf562c794efab237
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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