تفاعل #1361230

معادلة التفاعل

4-[(2-trimethylsiloxyethyl)ethylamino]trimethylsilylethynyl-benzene

tetrabutylammonium fluoride

Ethyl ether

→

viscous yellow oil

المردود 88.1%

4-[(2-Hydroxyethyl)ethylamino]-ethynylbenzene

المردود 88.1%

المذيبات

methanol THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared in the previous step
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   استخلاصthe mixture was extracted with water
4. 4
   أخرىThe organic layer was separated
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   أخرىthe solvent was removed under reduced pressure
7. 7
   أخرىchromatographed on silica gel with 35% ethyl acetate-hexane

الإجراء التجريبي

To a solution of 5.0 g, that is 15 mmole of 4-[(2-trimethylsiloxyethyl)ethylamino]trimethylsilylethynyl-benzene, prepared in the previous step, dissolved in 60 mL of methanol-THF (1:1) mixture, 33 ml, that is 33 mmole, of 1M tetrabutylammonium fluoride in THF, from Aldrich Chemical Co. was added dropwise. The solution was stirred at room temperature for 1 hour. Ethyl ether was added and the mixture was extracted with water. The organic layer was separated, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was flash column chromatographed on silica gel with 35% ethyl acetate-hexane to produce 2.5 g of a viscous yellow oil at an 88% yield.

المصدر