反応 #79367

反応方程式

tetrahydro-4H-pyran-4-one

magnesium

4-benzyloxy bromobenzene

→

4-(4-benzyloxyphenyl)tetrahydro-2H-pyran-4-ol

収率 55.1%

溶媒

THF

反応条件

後処理

1. 1
   その他In a 100 ml round-bottomed flask was placed
2. 2
   その他over 15 min
3. 3
   温度with occasional heating by a heat gun
4. 4
   workup.ADDITIONAfter the addition
5. 5
   温度upon cooling in an ice-water bath
6. 6
   workup.STIRRINGAfter stirring for 30 min
7. 7
   その他the solvent was removed under reduced pressure
8. 8
   workup.ADDITIONdiluted with AcOEt and sat. NH4Cl aq. The organic phase
9. 9
   その他was separated
10. 10
    濃縮concentrated
11. 11
    その他chromatographed on silica gel eluting with 40% AcOEt/hexanes

実験手順

In a 100 ml round-bottomed flask was placed magnesium turnings (1.85 g, 76.1 mmol), which was stirred under vacuum without solvent overnight. To it were slowly added anhydrous THF 40 ml and 4-benzyloxy bromobenzene (10 g, 38 mmol) over 15 min with occasional heating by a heat gun to keep the Grignard reagent formation going. After the addition was complete, the resulting gray slurry was stirred for 1 hr at 60° C. To it was added tetrahydro-4H-pyran-4-one (3.5 ml, 38 mmol) upon cooling in an ice-water bath. After stirring for 30 min, the solvent was removed under reduced pressure and diluted with AcOEt and sat. NH4Cl aq. The organic phase was separated, concentrated, and chromatographed on silica gel eluting with 40% AcOEt/hexanes to give 4-(4-benzyloxyphenyl)tetrahydro-2H-pyran-4-ol 5.95 g (55%).

出典