Reacción #73981

Ecuación de reacción

(E)-3-(3,5-difluoro-4-phenoxyphenyl)-2-methylprop-2-en-1-ol

Intermediate 93.1

(E)-3-(3,5-difluoro-4-phenoxyphenyl)-2-methylprop-2-en-1-ol

PPh3

phthalimide

diethyl azodicarboxylate

→

title compound

Rendimiento 63.0%

(E)-2-(3-(3,5-difluoro-4-phenoxyphenyl)-2-methylallyl)isoindoline-1,3-dione

Rendimiento 63.0%

Disolventes

EtOAc

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   Lavadothe organic layer was washed with water (2×30 mL), brine (30 mL)
3. 3
   Secadodried over Na2SO4
4. 4
   OtroAfter removal of solvent

Procedimiento

To a solution of (E)-3-(3,5-difluoro-4-phenoxyphenyl)-2-methylprop-2-en-1-ol (Intermediate 93.1) (410 mg, 1.49 mmol) in dry toluene (7.45 mL) under N2 was added PPh3 and phthalimide. The resulting solution was cooled to 0° C. and diethyl azodicarboxylate (DEAD, 0.748 mL) was added dropwise over several minutes. The reaction was allowed to warm to room temperature and stirred overnight. After diluting with EtOAc (20 mL), the organic layer was washed with water (2×30 mL), brine (30 mL) and dried over Na2SO4. After removal of solvent, the resulting residue was applied to a silica gel column (15% EtOAc in hexanes) to yield 385 mg of the title compound (63%) as an oil.

Fuente