Reaktion #170262

Reaktionsgleichung

triethylamine

1-benzhydrylazetidin-3-ol

DMSO

oxalyl chloride

→

1-benzhydrylazetidin-3-one

Ausbeute 105.0%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigeto reach 0° C.
3. 3
   Sonstigewas quenched with saturated NH4Cl (150 mL)
4. 4
   Extraktionextracted with DCM (3×)
5. 5
   WaschenThe combined organic layers were washed with water, brine
6. 6
   Sonstigedried on Na2SO4
7. 7
   Einengenconcentrated

Vorschrift

To a stirring solution of DMSO (12.45 ml, 176 mmol) in DCM (150 mL) at −78° C. under an argon atmosphere was added dropwise oxalyl chloride (8.61 mL, 100 mmol). After stirring for 30 minutes at −78° C., a solution of 1-benzhydrylazetidin-3-ol (20 g, 84 mmol) in DCM (75 mL) was added dropwise. The reaction mixture was stirred for 1 h at −78° C. before triethylamine (58.2 ml, 418 mmol) was added. The reaction mixture was allowed to reach 0° C. and was quenched with saturated NH4Cl (150 mL), and then extracted with DCM (3×). The combined organic layers were washed with water, brine, dried on Na2SO4 and concentrated to give crude 1-benzhydrylazetidin-3-one (20.8 g, 105%) as a yellow solid.

Quelle