Ethyl formate → HCID 57144783, compound

HRID 569911Notes

Reaction equation

HRID 569911 reaction equation
[CH3:1][N:2]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:5]=2[CH:4]=[N:3]1.[H-].[Na+].[CH:15](OCC)=[O:16]>C(O)C.O1CCCC1>[OH:16][CH:15]=[C:10]1[C:11](=[O:12])[C:5]2[CH:4]=[N:3][N:2]([CH3:1])[C:6]=2[CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 20146596115309-88-1

Product 1

HCID 57144783HCID 57144783, compound

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7 grams of 5,6,7,8-tetrahydro-1-methyl4(1H)-cycloheptapyrazolone, 2.3 grams of sodium hydride (97%), 12 ml of ethyl formate, 2 drops of ethanol and 100 ml of tetrahydrofuran was heated at reflux for 3 hours. The mixture was then cooled and partitioned between water and ether. The aqueous layer was washed once with ether and acidified to a pH of 5 with 1 N hydrochloric acid. The white precipitate which formed was separated by filtration and dried to give 5,6,7,8-tetrahydro-5-hydroxymethylene-1-methyl-4(1H)-cycloheptapyrazolone as a cream colored powder melting at about 133°-135° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was then cooled
  4. custompartitioned between water and ether
  5. washThe aqueous layer was washed once with ether
  6. customThe white precipitate which formed
  7. customwas separated by filtration
  8. customdried

Sources & evidence

ORD record
ord-8bb048309e6e435f9e9ef975be0f0aac
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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