2,5-Dimethoxytetrahydrofuran → methyl 3-(1H-pyrrol-1-yl)thiophene-2-carboxylate

HRID 1779479Notes

Reaction equation

HRID 1779479 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])[CH:13]=[CH:17][CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 522560methyl 3-(1H-pyrrol-1-yl)thiophene-2-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At room temperature, add 20 g (0.127 mol) of methyl 3-aminothiophene-2-carboxylate in small portions to a solution of 16.80 g (0.127 mol) of 2,5-dimethoxytetrahydrofuran in 100 ml of acetic acid. After 30 minutes' stirring at room temperature, then 90 minutes at 90° C., the acetic acid is removed under reduced pressure and the residue is taken up in 100 ml of 2N sodium hydroxide solution and extracted with diethyl ether. After washing with water and rendering colourless with animal charcoal, the ethereal phase is concentrated to dryness to yield the title compound.

Workup

  1. custom90 minutes at 90° C., the acetic acid is removed under reduced pressure
  2. extractionextracted with diethyl ether
  3. washAfter washing with water
  4. concentrationthe ethereal phase is concentrated to dryness

Sources & evidence

ORD record
ord-2b736dcb24834606811c1c8b0d604368
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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