Ethyl formate → 1-benzyl1,5,6,7-tetrahydro-5-hydroxymethylene 4H-indazol-4-one

HRID 569908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 569908
[CH2:1]([N:8]1[C:16]2[CH2:15][CH2:14][CH2:13][C:12](=[O:17])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:20](OCC)=[O:21].O1CCCC1>C(O)C.C(OCC)C.O>[CH2:1]([N:8]1[C:16]2[CH2:15][CH2:14][C:13](=[CH:20][OH:21])[C:12](=[O:17])[C:11]=2[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 8025Ethyl formateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 47385581-benzyl-1,5,6,7-tetrahydro-4H-indazol-4-one

Produkt 1

HCID 571673511-benzyl1,5,6,7-tetrahydro-5-hydroxymethylene 4H-indazol-4-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 7.8 grams of 1-benzyl-1,5,6,7-tetrahydro-4H-indazol-4-one, 2.8 grams of sodium hydride (60% suspension in mineral oil), 10 ml of ethyl formate, 2 drops of ethanol and 100 ml of tetrahydrofuran was stirred at reflux for 1 hour and then cooled. Water (300 ml) and 100 ml of ethyl ether were added and the mixture was stirred briefly. The layers were separated and the aqueous layer was washed with ethyl ether and acidified with concentrated hydrochloric acid to a pH of about 4. The resulting slurry was extracted several times with dichloromethane and the combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to give 1-benzyl1,5,6,7-tetrahydro-5-hydroxymethylene 4H-indazol-4-one as an amber oil.

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. stirringthe mixture was stirred briefly
  4. customThe layers were separated
  5. washthe aqueous layer was washed with ethyl ether
  6. extractionThe resulting slurry was extracted several times with dichloromethane
  7. dry with materialthe combined organic extracts were dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-19f96bb143b64f6b9a8f0978546ca404
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04734430

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