Reaktion #170119

Reaktionsgleichung

1-Iodopentane

1-diphenylmethylazetidin-3-ol

t-BuOK

→

title compound

Ausbeute 69.0%

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

Ausbeute 69.0%

Lösungsmittel

H2O

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturthen cooled to 0° C
3. 3
   workup.STIRRINGthe solution was stirred at room temperature for 18 h
4. 4
   Extraktionextracted twice with EtOAc
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated to dryness
7. 7
   SonstigeThe residue was purified on column chromatography (eluent: pentane/EtOAc, 95/5)

Vorschrift

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.

Quelle