Methanol → HCID 18945329, compound

HRID 399806Notes

Reaction equation

HRID 399806 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:16](=[O:22])[CH2:17]C(OC)=O)[CH:8]=[C:9]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[CH:10]=1)=[O:4].CO.S(=O)(=O)(O)O.C(OCC)(=O)C>O>[C:16]([C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[CH:8]=1)[C:3]([O:2][CH3:1])=[O:4])(=[O:22])[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 18945455HCID 18945455, compound

Product 1

HCID 18945329HCID 18945329, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of methyl 3-[3-methoxycarbonyl-5-(pyrrol-1-yl)phenyl]-3-oxopropionate (0.1 g) in a mixture of water (1 ml), methanol (3 ml) and concentrated sulfuric acid (40 mg) was refluxed for 16 hours. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate (50 ml) and water (50 ml). The organic layer was successively washed with a saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo to afford methyl 3-acetyl-5-(pyrrol-1-yl)benzoate (20.1 mg).

Workup

  1. temperaturewas refluxed for 16 hours
  2. washThe organic layer was successively washed with a saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-fd1b72d5e9784c18b03b7570112483a9
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…