Reaktion #2075755

Reaktionsgleichung

acetic acid

sodium cyanoborohydride

5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthene-2-carbaldehyde

5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthene-2-carboxaldehyde

acetic acid

→

crude title compound

Ausbeute 84.0%

2-(7-Hydroxymethyl-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one

Ausbeute 84.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter a further 12 hours
2. 2
   Sonstigethe excess borohydride was quenched with acetone
3. 3
   SonstigeAfter evaporation in vacuo, saturated NaHCO3
4. 4
   workup.ADDITIONwas added
5. 5
   Extraktionfollowed by extraction into dichloromethane
6. 6
   TrocknenThe combined organic layers were dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe brown coloured solid was dried under vacuum at 50° C.

Vorschrift

To a suspension of 5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthene-2-carbaldehyde (2)(0.392 g, 0.97 mmol) in ethanol (7 mL) at room temperature was added sodium cyanoborohydride (121 mg, 1.93 mmol), followed by the addition of acetic acid (1 mL). After 5 hours, a second addition of acetic acid (1 mL) was made. After a further 12 hours, the excess borohydride was quenched with acetone. After evaporation in vacuo, saturated NaHCO3 was added, followed by extraction into dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The brown coloured solid was dried under vacuum at 50° C. to give the crude title compound (0.332 g, 84%) which was used without any further purification. m/z (LC-MS, ESP), RT=3.09 min, (M++1)=408.3

Quelle