反应 #1543056

反应方程式

Diisobutylaluminum hydride

ester

(3R,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexanecarboxylic Acid Methyl Ester

→

diol

收率 24.0%

[(3R,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexyl]methanol

收率 24.0%

溶剂

ether

ether

反应条件

后处理

1. 1
   其他quenched by the slow addition of 2N potassium sodium tartrate
2. 2
   温度The solution was warmed to room temperature
3. 3
   workup.STIRRINGstirred for 15 min
4. 4
   workup.ADDITIONpoured into brine
5. 5
   萃取extracted with ethyl acetate and ether
6. 6
   洗涤washed
7. 7
   workup.ADDITIONwith diluted (ca. 1%) HCl, and brine
8. 8
   干燥dried (MgSO4)
9. 9
   其他evaporated
10. 10
    其他The crystalline residue was purified by flash chromatography
11. 11
    洗涤Elution with hexane/ethyl acetate (9:1)

实验过程

Diisobutylaluminum hydride (1.5M in toluene, 2.0 mL, 3 mmol) was added to a solution of the ester 3 (215 mg, 0.5 mmol) in anhydrous ether (3 mL) at -78° C. under argon. The mixture was stirred at -78° C. for 3 h and at -24° C. for 1.5 h, diluted with ether (10 mL) and quenched by the slow addition of 2N potassium sodium tartrate. The solution was warmed to room temperature and stirred for 15 min, then poured into brine and extracted with ethyl acetate and ether. The organic extracts were combined, washed with diluted (ca. 1%) HCl, and brine, dried (MgSO4) and evaporated. The crystalline residue was purified by flash chromatography. Elution with hexane/ethyl acetate (9:1) gave crystalline diol 4 (43 mg, 24%).

来源