반응 #340758

반응 방정식

phosphonium

THF

n-BuLi

dihydro-2H-pyran-4(3H)-one

→

product

수율 61.0%

3-(2H-pyran-4(3H,5H,6H)-ylidene)propan-1-ol

수율 61.0%

반응 조건

후처리

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued at rt overnight
3. 3
   기타The mixture was quenched with satd aq NH4Cl
4. 4
   여과filtered
5. 5
   건조The filtrate was dried over Na2SO4
6. 6
   농축concentrated under vacuum
7. 7
   기타to give the crude product, which
8. 8
   기타was purified by column chromatography

실험 절차

To a suspension of the phosphonium salt (90.2 g, 1.5 eq) in dry THF (1100 mL) at 0° C. under nitrogen atmosphere was added n-BuLi (2.5 M, 216 mL, 0.54 mol). The solution was stirred for 1 h, followed by addition of dihydro-2H-pyran-4(3H)-one (15 g, 0.15 mol). Stirring was continued at rt overnight. The mixture was quenched with satd aq NH4Cl, and then filtered. The filtrate was dried over Na2SO4, and concentrated under vacuum to give the crude product, which was purified by column chromatography to give the product (13.1 g, 61%). 1H NMR (CD3OD) δ 2.1-2.3 (m, 6H), 2.5 (s, 1H), 3.5-3.7 (m, 6H), 5.1-5.2 (t, 1H).

출처