Reacción #1929052

Ecuación de reacción

sodium thiosulfate

16-hydroxyhexadecanoic acid

tetrahydrofurane

→

16-oxohexadecanoic acid sodium salt

Rendimiento 34.0%

Disolventes

sodium bicarbonate

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 1.5 hrs
2. 2
   ExtracciónIntermediate 1 was extracted with diethylether
3. 3
   Secadoafter drying over sodium sulfate the organic layer
4. 4
   Otrowas evaporated to dryness
5. 5
   Otropurified by column chromatography
6. 6
   Otroas separating agent
7. 7
   workup.ADDITIONa solvent mixture of toluene/ethylacetate

Procedimiento

To a cooled solution (0° C.) of 16-hydroxyhexadecanoic acid (800 mg, 2.9 mmol) in dichloromethane (10 ml) and tetrahydrofurane (20 ml) Dess-Martin periodinane (1636 mg, 3.7 mmol) was added at 0° C. The mixture was stirred for 3.5 hrs at 0° C. and 2.5 hrs at room temperature under Ar-atmosphere. Then a 15%-solution of sodium thiosulfate in saturated sodium bicarbonate solution was added, the mixture was stirred at room temperature for 1.5 hrs. Intermediate 1 was extracted with diethylether, after drying over sodium sulfate the organic layer was evaporated to dryness and purified by column chromatography using silica gel as separating agent and a solvent mixture of toluene/ethylacetate. Yield: 34% (white solid).

Fuente