Reaktion #56751

Reaktionsgleichung

water

Triethylamine

1-benzhydryl-azetidin-3-ol

pyridine sulfur trioxide

→

title compound

Ausbeute 170.6%

1-Benzhydryl-azetidin-3-one

Ausbeute 170.6%

Lösungsmittel

dimethylsulfoxide

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITfor 2 hours at room temperature
2. 2
   Extraktionextracted with methylene chloride (3×100 mL)
3. 3
   WaschenThe organic layer was washed with water (3×150 mL)
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under vacuum
7. 7
   Sonstigechromatographed on silica gel (30% ethyl acetate-hexane)
8. 8
   EinengenThe product-containing fractions were concentrated under vacuum

Vorschrift

Triethylamine (11.6 ml, 42 mmol) was added to a solution of 1-benzhydryl-azetidin-3-ol (2.0 g, 4.2 mmol) in dimethylsulfoxide (60 mL) at room temperature. The resulting mixture was cooled to 10° C., then pyridine sulfur trioxide (8.64 g, 33.6 mmol) in dimethylsulfoxide was introduced. The mixture was stirred at 10° C. for 1 hour and then for 2 hours at room temperature. The reaction mixture was poured into water (100 mL) and extracted with methylene chloride (3×100 mL). The organic layer was washed with water (3×150 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude oil was column chromatographed on silica gel (30% ethyl acetate-hexane). The product-containing fractions were concentrated under vacuum to give 1.7 g (86%) of the title compound as a yellow solid, m.p. 52-54° C.

Quelle