反応 #58887

反応方程式

1-(2-fluoro-4-hydroxy-phenyl)-ethanone

3,4-dihydro-2H-pyran

pyridinium p-toluenesulfonate

→

desired product

収率 74.0%

1-[2-Fluoro-4-(tetrahydro-pyran-2-yloxy)-phenyl]-ethanone

収率 74.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   洗浄The organic phase was washed with 1 N NaOH (aq) (1×50 mL)
2. 2
   乾燥dried (K2CO3)
3. 3
   その他Evaporation in vacuo
4. 4
   その他gave a brown oil, that
5. 5
   workup.DISTILLATIONwas purified by vacuum distillation

実験手順

A solution of 1-(2-fluoro-4-hydroxy-phenyl)-ethanone (130 mmol), 3,4-dihydro-2H-pyran (260 mmol) and a catalytic amount of pyridinium p-toluenesulfonate in CH2Cl2 (200 mL) was left overnight at room temperature. The organic phase was washed with 1 N NaOH (aq) (1×50 mL) and dried (K2CO3). Evaporation in vacuo gave a brown oil, that was purified by vacuum distillation. The desired product was isolated as clear oil in 74% yield: bp: 130-140 ° C./0.05 mbar. 1H-NMR (CDCl3) δ 7.86 (t, 1H), 6.87 (dd, 1H), 6.82 (dd, 1H), 5.49 (t, 1H), 3.86-3.78 (m, 1H), 3.67-3.61 (m, 1H), 2.59 (d, 3H), 1.97-1.60 (m, 6H).

出典