反応 #340758

反応方程式

phosphonium

THF

n-BuLi

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

→

product

収率 61.0%

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

収率 61.0%

反応条件

後処理

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued at rt overnight
3. 3
   その他The mixture was quenched with satd aq NH4Cl
4. 4
   ろ過filtered
5. 5
   乾燥The filtrate was dried over Na2SO4
6. 6
   濃縮concentrated under vacuum
7. 7
   その他to give the crude product, which
8. 8
   その他was purified by column chromatography

実験手順

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).

出典