Reaction #170241

Reaction equation

methanesulfonyl chloride

1-benzhydryl-3-(benzofuran-3-yl)azetidin-3-ol

triethylamine

→

crude title compound

1-Benzhydryl-3-(benzofuran-3-yl)-3-chloroazetidine

Solvents

dichloromethane

water

dichloromethane

Conditions

Workup

1. 1
   Extractionextracted with dichloromethane (3×50 mL)
2. 2
   DryingThe combined organic layers were dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated to dryness

Procedure

To a solution of 1-benzhydryl-3-(benzofuran-3-yl)azetidin-3-ol (760 mg, 2.14 mmol) in dichloromethane (10 mL) was added at 0° C. triethylamine (387 μL, 2.78 mmol) and then dropwise a solution of methanesulfonyl chloride (216 μL, 2.78 mmol) in dichloromethane (3 mL). The reaction mixture was stirred for 1 hour at room temperature, then diluted with water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The crude title compound was obtained as a yellow gum (873 mg, 109%) and used for the next step without further purification.

Source