Reacción #2025283

Ecuación de reacción

butyrylchloride

(+)-3-methyl-3-(4-benzyloxyphenyl)propanol

water

→

(+)-4-benzyloxy-1-(1-methyl-3-butyryloxypropyl)benzene

Rendimiento 95.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroreacted for 2 hours
2. 2
   Extracciónextracted with 200 ml of toluene
3. 3
   Otroseparated
4. 4
   Lavadowashed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water
5. 5
   Secadodried on anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONAfter the solvent was distilled out under the reduced pressure
7. 7
   Otrothe resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

Procedimiento

2.56 (10 millimols) of (+)-3-methyl-3-(4-benzyloxyphenyl)propanol (XI-1) obtained in Preparation Example (starting material compound (V)) 1, was dissolved in 20 ml of pyridine and 1.38 g (13 millimols) of butyrylchloride was added at 30°-40° C. and reacted for 2 hours. The reaction mixture was poured into 200 ml of water and extracted with 200 ml of toluene and separated and then washed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water, and thereafter dried on anhydrous magnesium sulfate. After the solvent was distilled out under the reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to provide 3.1 g (yield: 95%) of (+)-4-benzyloxy-1-(1-methyl-3-butyryloxypropyl)benzene (VIII-9).

Fuente