反応 #1773

反応方程式

trans-2-phenyl-1-cyclohexanol

diethyl azodicarboxylate

methyl 4-hydroxy-2-methoxybenzoate

triphenylphosphine

→

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

溶媒

THF

THF

反応条件

後処理

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

実験手順

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.

出典