Reacción #1773

Ecuación de reacción

trans-2-phenyl-1-cyclohexanol

diethyl azodicarboxylate

methyl 4-hydroxy-2-methoxybenzoate

triphenylphosphine

→

methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction was filtered
2. 2
   Otrothe solvent was removed under reduced pressure
3. 3
   OtroThe residue was chromatographed on a silica gel column
4. 4
   LavadoEtOAc and eluted with same
5. 5
   Otrothe solvent removed under reduced pressure

Procedimiento

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (310 mg, 1.7 mmol) in dry THF (1.25 mL) was added triphenylphosphine (446 mg, 1.7 mmol) and the solution was cooled to 0° C. A 500 mL volume of trans-2-phenyl-1-cyclohexanol (200 mg, 1.35 mmol) and diethyl azodicarboxylate (319 μL, 2.02 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 92:8 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate.

Fuente