Reacción #1770

Ecuación de reacción

tetrahydro-4H-pyran-4-ol

diethyl azodicarboxylate

methyl 4-hydroxy-2-methoxybenzoate

triphenylphosphine

→

methyl 4-(4-tetra-hydropyranoyloxy)-2-methoxy-benzoate

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 (713 mg, 3.92 mmol) in dry THF (7.5 mL) was added triphenylphosphine (1.42 g, 5.4 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of tetrahydro-4H-pyran-4-ol (466 mL, 4.90 mmol) and diethyl azodicarboxylate (850 μL, 5.4 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 60:40 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(4-tetra-hydropyranoyloxy)-2-methoxy-benzoate.

Fuente