Reaktion #82697

Reaktionsgleichung

sodium hydroxide

hydrogen peroxide

3-carbonylethoxy-5-methoxymethyl-isoxazole

L-selectride

→

product

3-Hydroxymethyl-5-methoxymethyl-isoxazole

Lösungsmittel

ethanol

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to 0° C
2. 2
   workup.STIRRINGAfter stirring for half an hour the supernatant
3. 3
   Sonstigewas decanted
4. 4
   Waschenthe residue washed several times with methylene chloride
5. 5
   ExtraktionThe aqueous phase was extracted with dichloromethane in an extraction apparatus for one day
6. 6
   TrocknenThe organic phase was dried over sodium sulfate
7. 7
   Sonstigethe solvent evaporated

Vorschrift

To a solution of 6.55 g of 3-carbonylethoxy-5-methoxymethyl-isoxazole in 70 ml dry tetrahydrofuran were added 77.6 ml of a 1 N solution of L-selectride® at 0° C. The solution was stirred overnight at room temperature. After cooling to 0° C. 13 ml of water and 33 ml of ethanol were added, then simultaneously 33 ml of a 6 N solution of sodium hydroxide and 49 ml hydrogen peroxide were added with caution. After stirring for half an hour the supernatant was decanted, the residue washed several times with methylene chloride. The aqueous phase was extracted with dichloromethane in an extraction apparatus for one day. The organic phase was dried over sodium sulfate and the solvent evaporated to give 4.1 g product.

Quelle