Reacción #4449

Ecuación de reacción

1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone

sodium borohydride

→

1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanol

Rendimiento 45.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated
2. 2
   workup.ADDITIONdiluted with water
3. 3
   Extracciónextracted with ether (3×25 mL)
4. 4
   LavadoThe combined extracts were washed with brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   Concentraciónconcentrated
7. 7
   Otrochromatographed
8. 8
   OtroRecrystallization from hexane/ethyl acetate

Procedimiento

To a solution of 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (675 g, 0.0025 mol) in methanol (40 mL) was added sodium borohydride (300 mg, 0.0079 mol) in portions and the mixture allowed to stir at room temperature for one hour. The reaction mixture was concentrated, diluted with water, and extracted with ether (3×25 mL). The combined extracts were washed with brine, dried over magnesium sulfate, concentrated, and chromatographed. Recrystallization from hexane/ethyl acetate afforded 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanol (300 mg, 45%). mp. 146°-147° C.

Fuente