Reaction #82697

Reaction equation

sodium hydroxide

hydrogen peroxide

3-carbonylethoxy-5-methoxymethyl-isoxazole

L-selectride

→

product

3-Hydroxymethyl-5-methoxymethyl-isoxazole

Solvents

ethanol

water

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter cooling to 0° C
2. 2
   workup.STIRRINGAfter stirring for half an hour the supernatant
3. 3
   Otherwas decanted
4. 4
   Washthe residue washed several times with methylene chloride
5. 5
   ExtractionThe aqueous phase was extracted with dichloromethane in an extraction apparatus for one day
6. 6
   DryingThe organic phase was dried over sodium sulfate
7. 7
   Otherthe solvent evaporated

Procedure

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.

Source