반응 #79367

반응 방정식

tetrahydro-4H-pyran-4-one

magnesium

4-benzyloxy bromobenzene

→

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

수율 55.1%

용매

THF

반응 조건

후처리

1. 1
   기타In a 100 ml round-bottomed flask was placed
2. 2
   기타over 15 min
3. 3
   온도with occasional heating by a heat gun
4. 4
   workup.ADDITIONAfter the addition
5. 5
   온도upon cooling in an ice-water bath
6. 6
   workup.STIRRINGAfter stirring for 30 min
7. 7
   기타the solvent was removed under reduced pressure
8. 8
   workup.ADDITIONdiluted with AcOEt and sat. NH4Cl aq. The organic phase
9. 9
   기타was separated
10. 10
    농축concentrated
11. 11
    기타chromatographed on silica gel eluting with 40% AcOEt/hexanes

실험 절차

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%).

출처