反応 #170119

反応方程式

1-Iodopentane

1-diphenylmethylazetidin-3-ol

t-BuOK

→

title compound

収率 69.0%

1-(Diphenylmethyl)-3-(pentyloxy)azetidine

収率 69.0%

溶媒

H2O

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   温度then cooled to 0° C
3. 3
   workup.STIRRINGthe solution was stirred at room temperature for 18 h
4. 4
   抽出extracted twice with EtOAc
5. 5
   乾燥dried over Na2SO4
6. 6
   濃縮concentrated to dryness
7. 7
   その他The residue was purified on column chromatography (eluent: pentane/EtOAc, 95/5)

実験手順

A solution of 1-diphenylmethylazetidin-3-ol (300 mg, 1.25 mmol) in THF (4.5 mL) was cooled to 0° C. t-BuOK (1M in THF, 3.75 mL) was added dropwise and the reaction mixture was stirred at room temperature for 1 h then cooled to 0° C. 1-Iodopentane (816 μL, 6.25 mmol) was added and the solution was stirred at room temperature for 18 h. The reaction mixture was diluted with H2O and extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to dryness. The residue was purified on column chromatography (eluent: pentane/EtOAc, 95/5) to give the title compound (267 mg, 69%) as a clear oil.

出典