Ethyl 2-oxocyclopentanecarboxylate → 87753-08-0

HRID 1768519Notes

Reaction equation

HRID 1768519 reaction equation
C([O-])(=O)C.[Na+].CCO[C:9]([CH:11]1[C:15](=O)[CH2:14][CH2:13][CH2:12]1)=[O:10].Cl.[C:18]([NH2:26])(=[NH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C(C)=CC=CC=1>[C:19]1([C:18]2[NH:26][C:9](=[O:10])[C:11]3[CH2:12][CH2:13][CH2:14][C:15]=3[N:25]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 80289Benzamidine, hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 13575338987753-08-0Yield 37%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 15.6 g (190 mmol) of sodium acetate, 25 mL (172.7 mmol) of ethyl cyclopentanone-2-carboxylate, 27.7 g (177 mmol) of benzamidine hydrochloride and 250 mL of xylene was refluxed with a Dean Stark trap for 8 hours. Most of the xylene was distilled off and the hot reaction mixture was poured onto crushed ice. The reaction mixture was left to stand at room temperature for 0.5 hour, then vacuum filtered to remove the product, as a gray solid. The solid was air dried overnight to yield 13.35 g (37.0%) of 2-phenyl-3,5,6,7-tetrahydro-4H-cyclopentapyrimidin-4-one. 1H-NMR (CDCl3) δ2.11 (2H,m), 2.90 (4H,m), 7.5 (3H,m), 8.18 (2H,m).

Workup

  1. temperaturewas refluxed with a Dean Stark trap for 8 hours
  2. distillationMost of the xylene was distilled off
  3. additionthe hot reaction mixture was poured
  4. customonto crushed ice
  5. waitThe reaction mixture was left
  6. filtrationvacuum filtered
  7. customto remove the product
  8. customdried overnight

Sources & evidence

ORD record
ord-6f76cc1a65e24ef480a749ed257a62c6
Source dataset
uspto-grants-1995_01
Patent number
US05378678

Reaction notes

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