Reaktion #638909

Reaktionsgleichung

benzoic acid

triphenylphosphine

(2R,4R)-2,4-pentanediol

azodicarboxylic acid bis(2-methoxyethyl) ester

→

(4S,2R)-4-benzoyloxypentane-2-ol

benzoic acid

Lösungsmittel

THF

Water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Sonstigeat 20° C.
3. 3
   Einengenconcentration
4. 4
   workup.ADDITIONThen, water (10 ml) was added to the solution, and extraction
5. 5
   WaschenThen, the organic layer was washed with water (10 ml) and saturated salt water (10 ml)
6. 6
   SonstigeSubsequently, a crude product obtained by concentration
7. 7
   Sonstigewas purified by column chromatography (silica gel, 40% ethyl acetate-hexane solution)

Vorschrift

After benzoic acid (300 mg, 2.46 mmol), triphenylphosphine (775 mg, 2.95 mmol), (2R,4R)-2,4-pentanediol (308 mg, 2.95 mmol), and THF (12 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (691.1 mg, 2.95 mmol) dissolved in THF (6 mL) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for one hour. Water (0.5 ml) was added, and concentration was carried out. Then, water (10 ml) was added to the solution, and extraction was 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, 40% ethyl acetate-hexane solution) to give (4S,2R)-4-benzoyloxypentane-2-ol as a colorless oily substance (379 mg, yield: 74%/benzoic acid).

Quelle