Reaktion #336343

Reaktionsgleichung

methyl 3-(chloromethyl)benzoate

10,11-dihydro-5H-dibenz[b,f]azepine

potassium tert-butoxide

→

methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate

Ausbeute 25.6%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at 25° C. for 1 hour
2. 2
   Sonstigeevaporated
3. 3
   SonstigeThe residue was partitioned between ethyl acetate and 0.1N hydrochloric acid
4. 4
   WaschenThe organic layer was washed with water and brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (40:1)

Vorschrift

To a solution of 10,11-dihydro-5H-dibenz[b,f]azepine (2.44 g) in tetrahydrofuran (25 ml) was added potassium tert-butoxide (2.02 g) at 0° C. The mixture was stirred at 0° C. for 15 minutes, and then a solution of methyl 3-(chloromethyl)benzoate (3.57 g) in tetrahydrofuran (15 ml) was added. The mixture was stirred at 25° C. for 1 hour, and then evaporated. The residue was partitioned between ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (40:1) to give methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate (1.10 g) as an oil.

Quelle