반응 #50179

반응 방정식

4-methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran

RED-AL

→

4-methoxy-4-(3-hydroxy -trans-prop-1-enyl)tetrahydropyran

수율 48.0%

용매

THF

반응 조건

후처리

1. 1
   기타The cooling bath was removed
2. 2
   기타quenched by addition of crushed ice and saturated aqueous NH4Cl
3. 3
   추출The resulting two-phase mixture was extracted with ethyl acetate (4×90 mL)
4. 4
   건조The combined organic layers were dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타Purification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes)

실험 절차

A solution of 4-methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran (10.8 g, 44.9 mmol), prepared as in step 3, in dry THF (100 mL) was cooled to -75° C., and RED-AL (sodium bis(2-methoxyethoxy)aluminum hydride, Aldrich Chemical Co., 20 mL of 3.4M solution in toluene, 68 mmol) was added under a dry argon atmosphere. The cooling bath was removed and the reaction was warmed to 0° C. and quenched by addition of crushed ice and saturated aqueous NH4Cl. The resulting two-phase mixture was extracted with ethyl acetate (4×90 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes) provided 4-methoxy-4-(3-hydroxy -trans-prop-1-enyl)tetrahydropyran(3.71 g, 34 %) as a colorless oil.

출처