Reacción #520227

Ecuación de reacción

Triphenylphosphine

compound 11

4-Benzyloxy-3-fluorobenzoic Acid

(S)-(+)-octan-2-ol

diethyl azodicarboxylate

→

(R)-(−)-1-Methyheptyl 4-Benzyloxy-3-fluorobenzoate

Disolventes

dichloromethane

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITThe reaction solution was left
2. 2
   OtroUpon completion, the solvent was removed in vacuo
3. 3
   Otroto yield a colourless solid which
4. 4
   Otrowas purified by column chromatography (dichloromethane) on silica
5. 5
   Otroto yield a colourless oil
6. 6
   Otroat 25° C.

Procedimiento

Triphenylphosphine (7.92 g, 30 mmol) in THF (40 ml) was added dropwise to a stirred solution of compound 11 (7.00 g, 28 mmol), (S)-(+)-octan-2-ol (3.66 g 28 mmol) and diethyl azodicarboxylate (4.87 g, 28 mmol) in THF (100 ml). The reaction solution was left stirring under nitrogen until completion [reaction monitored by TLC (dichloromethane, silica)]. Upon completion, the solvent was removed in vacuo to yield a colourless solid which was purified by column chromatography (dichloromethane) on silica to yield a colourless oil. Yield 10.01 g (99%), [α]D=−22.4° at 25° C.

Fuente