Ethyl formate → HCID 57200472, compound

HRID 569912Notes

Reaction equation

HRID 569912 reaction equation
[H-].[Na+].C([O:5][CH2:6][CH3:7])=O.[CH2:8]([N:15]1[C:19]2[CH2:20]C[C:22](=[O:23])[C:18]=2[CH:17]=[N:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C.O1CCCC1.O>[CH2:8]([N:15]1[C:19]2[CH2:20][C:7](=[CH:6][OH:5])[C:22](=[O:23])[C:18]=2[CH:17]=[N:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 8025Ethyl formate2×HCID 24758Sodium hydride2×HCID 141267231-benzyl-5,6-dihydro-4(1H)-cyclopentapyrazolone

Product 1

HCID 57200472HCID 57200472, compound

Reagents, catalysts & solvents 3

HCID 702EthanolCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (1.44 grams of a 60% suspension in mineral oil), 1.46 ml of ethyl formate and 3 drops of ethanol were combined in 150 ml of anhydrous tetrahydrofuran and stirred at room temperature for 30 minutes. A solution of 4 grams of 1-benzyl-5,6-dihydro-4(1H)-cyclopentapyrazolone in 50 ml of anhydrous tetrahydrofuran was added dropwise and the reaction mixture was heated at reflux for 16 hours. An additional 1.44 grams of sodium hydride suspension and 1.46 ml of ethyl formate were then added and the reaction mixture was heated at reflux for 2 hours. The mixture was cooled, diluted with 150 ml of water, and washed with ethyl ether. The aqueous layer was acidified with aqueous hydrochloric acid and the solid which formed was collected by filtration to give 1-benzyl-5,6-dihydro-5-hydroxymethylene-4(1H)-cyclopentapyrazolone as a tan solid melting at about 171°-172° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 2 hours
  5. temperatureThe mixture was cooled
  6. washwashed with ethyl ether
  7. customthe solid which formed
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-16c6cf3cf5e84d27934c801ebfb1519b
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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