반응 #2467697

반응 방정식

trimethylsilylchloride

2-tetradecanone

triethylamine

sodium bicarbonate

diisopropylamine

n-butyl lithium

→

2-[(Trimethylsilyl)oxy]-1-tetradecene

용매

—

petroleum ether

THF

THF

—

hexanes

반응 조건

후처리

1. 1
   workup.STIRRINGStirred 5 minutes
2. 2
   온도to warm
3. 3
   기타reached 0° C.
4. 4
   세척the organic layer was washed with chilled H2O (2×1.4 L)
5. 5
   온도chilled 0.1M citric acid (3× 2 L) and saturated NaCl
6. 6
   건조The organic layer was dried (Na2SO4)
7. 7
   기타dried in vacuo
8. 8
   기타to give a yellow oil

실험 절차

To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3× 2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%).

출처