反应 #1770

反应方程式

tetrahydro-4H-pyran-4-ol

diethyl azodicarboxylate

methyl 4-hydroxy-2-methoxybenzoate

triphenylphosphine

→

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

溶剂

THF

THF

反应条件

后处理

1. 1
   过滤The reaction was filtered
2. 2
   其他the solvent was removed under reduced pressure
3. 3
   其他The residue was chromatographed on a silica gel column
4. 4
   洗涤EtOAc and eluted with same
5. 5
   其他the solvent removed under reduced pressure

实验过程

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.

来源