반응 #460355

반응 방정식

n-butyllithium

2-tridecanone

diisopropylamine

chlorotrimethylsilane

→

title compound

수율 99.1%

2-trimethylsilyloxy-1-tridecene

수율 99.1%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting mixture was stirred (30 minutes, -78° C.)
2. 2
   기타The dry ice bath was removed
3. 3
   기타quenched with saturated sodium bicarbonate (100 mL)
4. 4
   workup.ADDITIONDichloromethane (400 mL) and water (80 mL) were added
5. 5
   기타the layers were separated
6. 6
   세척The organic layer was washed with brine (1×200 mL)
7. 7
   건조dried (MgSO4)
8. 8
   농축concentrated in vacuo

실험 절차

A solution of n-butyllithium (12.6 mL, 27.7 mmol, 2.2 M in hexane) was added dropwise via syringe to a cooled (-78° C.) solution of diisopropylamine (4.1 mL, 29 mmol) in dry THF (200 mL). The resulting solution was stirred (15 minutes -78° C.), then a solution of 2-tridecanone (5.0 g, 25 mmol) in dry THF (50 mL) was added dropwise via a drop-in funnel. The resulting mixture was stirred (30 minutes, -78° C.), then a solution of chlorotrimethylsilane (3.5 mL, 28 mmol) in dry THF (40 mL) was added in one portion. The dry ice bath was removed and the resulting mixture was warmed to 10° C., then quenched with saturated sodium bicarbonate (100 mL). Dichloromethane (400 mL) and water (80 mL) were added and the layers were separated. The organic layer was washed with brine (1×200 mL), dried (MgSO4), and concentrated in vacuo to yield 6.7 g (98%) of the title compound as a milky oil which was used without further purification.

출처