Reacción #2348469

Ecuación de reacción

hydrochloric acid

sodium methoxide

hydroxylamine hydrochloride

2,2-dimethyl-6-(tetrahydro-2H-pyran-2-yloxy)-4-hexyn-3-one

sodium hydrogen carbonate

→

(3-t-butyl-isoxazol-5-yl)methanol

Rendimiento 36.1%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 18 hours
3. 3
   Extracciónthe reaction mixture was extracted with ethyl acetate
4. 4
   LavadoThe extract was washed with aqueous saturated sodium chloride
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure

Procedimiento

4.49 g of 2,2-dimethyl-6-(tetrahydro-2H-pyran-2-yloxy)-4-hexyn-3-one was dissolved in 20 ml of methanol, and 1.30 g of sodium methoxide and 1.53 g of hydroxylamine hydrochloride were added. The mixture was stirred at 70° C. for 2 hours. The reaction mixture was cooled to room temperature and then adjusted to pH 2 with concentrated hydrochloric acid. The mixture was stirred at room temperature for 18 hours. After aqueous saturated sodium hydrogen carbonate was added, the reaction mixture was extracted with ethyl acetate. The extract was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.12 g of (3-t-butyl-isoxazol-5-yl)methanol.

Fuente