Pyrrolidine → Dimethyl 3,4-Dihydro-2,2-dimethyl-4-oxo-2H-1-benzopyran-6,7-dicarboxylate

HRID 36873Notes

Reaction equation

HRID 36873 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:15]([O:17][CH3:18])=[O:16])[C:7](=[CH:12][C:13]=1[OH:14])[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2].N1C[CH2:22][CH2:21][CH2:20]1>CC(C)=O>[CH3:20][C:21]1([CH3:22])[CH2:2][C:1](=[O:3])[C:4]2[CH:5]=[C:6]([C:15]([O:17][CH3:18])=[O:16])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][C:13]=2[O:14]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 13227611Dimethyl 4-acetyl-5-hydroxyphthalate

Product 1

HCID 19936389Dimethyl 3,4-Dihydro-2,2-dimethyl-4-oxo-2H-1-benzopyran-6,7-dicarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 100 ml of acetone was dissolved 4.2 g of dimethyl 4-acetyl-5-hydroxyphthalate synthesized in accordance with the process of Bulletin of the Chemical Society of Japan, Vol. 57, p. 3221 (1984). To the solution were added 1.0 ml of pyrrolidine and a small amount of Molecular Sieve (3A), followed by stirring at room temperature for 3 days. Any insoluble material was removed by filtration, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4.6 g (86.3%) of a yellow oily substance.

Workup

  1. customsynthesized in accordance with the process of Bulletin of the Chemical Society of Japan, Vol. 57, p
  2. customAny insoluble material was removed by filtration
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. customto obtain 4.6 g (86.3%) of a yellow oily substance

Sources & evidence

ORD record
ord-6f7e69cbea9b4ca2a006d71718374361
Source dataset
uspto-grants-1995_05
Patent number
US05418232

Reaction notes

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