Reacción #638927

Ecuación de reacción

(S)-2-octanol

triphenylphosphine

4-nitrobenzoic acid

azodicarboxylic acid bis(2-methoxyethyl) ester

→

(S)-2-octanol

(R)-2-(4-nitrobenzoyloxy)octane

Disolventes

dichloromethane

Water

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Otroat 20° C.
3. 3
   Otroseparation
4. 4
   ExtracciónThen, the aqueous layer was extracted
5. 5
   LavadoThe resulting organic layer was collectively washed with water (10 mL) and saturated salt water (10 ml)
6. 6
   OtroSubsequently, a crude product obtained by concentration
7. 7
   Otrowas purified by column chromatography (silica gel, 5% ethyl acetate-hexane solution)

Procedimiento

After (S)-2-octanol (300 mg, 2.30 mmol), triphenylphosphine (726 mg, 2.76 mmol), 4-nitrobenzoic acid (462 mg, 2.76 mmol), and dichloromethane (12 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (648 mg, 2.76 mmol) dissolved in dichloromethane (6 ml) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for 1.5 hours. Water (10 mL) was added, and separation was carried out. Then, the aqueous layer was extracted using dichloromethane (10 mL, ×1). The resulting organic layer was collectively washed with water (10 mL) and saturated salt water (10 ml), and dehumidified with anhydrous magnesium sulfate. Subsequently, a crude product obtained by concentration was purified by column chromatography (silica gel, 5% ethyl acetate-hexane solution) to give (R)-2-(4-nitrobenzoyloxy)octane as a pale yellow liquid substance (572 mg, yield: 89%/(S)-2-octanol).

Fuente