Reaktion #2358254

Reaktionsgleichung

tetrabutylammonium fluoride

4,5-epoxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepine

N-methyl-N-trimethylsilylethanesulfonamide

→

trans-7-nitro-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol

Ausbeute 74.2%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONpoured onto ammonium chloride solution
2. 2
   ExtraktionIt was extracted several times with EA
3. 3
   Waschenthe organic phase was washed with water
4. 4
   Trocknendried over sodium sulfate
5. 5
   EinengenAfter concentration and recrystallization of the solid residue from isopropanol

Vorschrift

2 g of tetrabutylammonium fluoride were added with stirring to a mixture of 6 g of 4,5-epoxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepine and 9.5 g of N-methyl-N-trimethylsilylethanesulfonamide. The reaction mixture was then heated for 3 h at 65° C., stirred overnight at RT and poured onto ammonium chloride solution. It was extracted several times with EA, and the organic phase was washed with water and dried over sodium sulfate. After concentration and recrystallization of the solid residue from isopropanol, 7.1 g of trans-7-nitro-5-(N-ethylsulfonyl-N-methylamino)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol were obtained, m.p. 133-135° C.

Quelle