반응 #53616

반응 방정식

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

수율 69.0%

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

수율 69.0%

용매

ammonium chloride

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

출처