Reacción #638925

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

THF

Water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Otroat 20° C.
3. 3
   Concentraciónconcentration
4. 4
   workup.ADDITIONThen, water (10 ml) was added to the solution, and extraction
5. 5
   LavadoThen, the organic layer was 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, 10% 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 THF (12 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (648 mg, 2.76 mmol) dissolved in THF (6 ml) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for 2.5 hours. Water (0.5 mL) was added, and concentration was carried out. Then, water (10 ml) was added to the solution, and extraction was then carried out using diethyl ether (10 ml, ×2). Then, the organic layer was 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, 10% ethyl acetate-hexane solution) to give (R)-2-(4-nitrobenzoyloxy)octane as a pale yellow liquid substance (579 mg, yield: 90%/(S)-2-octanol).

Fuente