تفاعل #53616

معادلة التفاعل

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

المردود 69.0%

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

المردود 69.0%

المذيبات

ammonium chloride

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر