反応 #53616

反応方程式

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

収率 69.0%

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

収率 69.0%

溶媒

ammonium chloride

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise to the solution
2. 2
   workup.STIRRINGthe mixture was stirred for 2 h
3. 3
   その他The reaction mixtures
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄The extracts were washed with brine
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The residue obtained
9. 9
   その他was chromatographed on aluminum oxide in ethyl acetate:hexane (1:5)

実験手順

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.

出典