Reaktion #53616

Reaktionsgleichung

dimethyldisulfide

compound ( 42 )

(5-Bromo-2-triisopropylsilanyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine

n-BuLi

→

titled compound

Ausbeute 69.0%

Dimethyl-(5-methylsulfanyl-2-triisopropylsilanyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulen-8-yl)amine

Ausbeute 69.0%

Lösungsmittel

ammonium chloride

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise to the solution
2. 2
   workup.STIRRINGthe mixture was stirred for 2 h
3. 3
   SonstigeThe reaction mixtures
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe extracts were washed with brine
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue obtained
9. 9
   Sonstigewas chromatographed on aluminum oxide in ethyl acetate:hexane (1:5)

Vorschrift

A solution of compound (42) 451 mg in dry tetrahydrofuran 5 ml was cooled at −70° C. n-BuLi (1.56 mol/l hexane solution) 1.3 ml was added dropwise to the solution and the mixture was stirred for 1 h. Then, dimethyldisulfide 185 μl was added and the mixture was stirred for 2 h. The reaction mixtures was diluted with an aqueous ammonium chloride solution and extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in ethyl acetate:hexane (1:5) to give the titled compound as colorless crystals, 289.8 mg. Yield 69%. This was recrystallized from hexane to give the titled compound as colorless crystals, m.p. 77-79° C.

Quelle