Reaktion #322452

Reaktionsgleichung

8-acetyl-4,4a, 5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one

sodium borohydride

→

8-(1-hydroxyethyl)-4,4a,5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one

Ausbeute 43.6%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   EinengenThe mixture was concentrated in vacuo until about a half volume of the methanol
3. 3
   Sonstigewas evaporated
4. 4
   workup.ADDITIONwater was added
5. 5
   Extraktionextracted with chloroform
6. 6
   WaschenThe extract was washed with brine
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe residue was chromatographed on a silica gel (SiO2 :30 g) column
10. 10
    SonstigeThe resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane

Vorschrift

To a suspension of 1.3 g of 8-acetyl-4,4a, 5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in methanol was added 300 mg of sodium borohydride under ice-cooling and the mixture was stirred for 3 hours. The mixture was concentrated in vacuo until about a half volume of the methanol was evaporated and water was added, and then extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :30 g) column using a mixed solvent of chloroform and methanol (98:2) as an eluent. The resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane to give 570 mg of 8-(1-hydroxyethyl)-4,4a,5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a pale yellow powder, melting at 129°-145° C.

Quelle