Реакция #1816177

Уравнение реакции

water

NaOH

water

(R/S)-2-methyl-4-[(1S,2R,3S,5S)-3-pinanyl]butanal

LiAlH4

→

(R/S)-2-methyl-4-[(1S,2R,3S,5S)-3-pinanyl]-1-butanol

Выход 81.0%

Растворители

—

same solvent

ethyl ether

ethyl ether

Условия реакции

Обработка

1. 1
   workup.ADDITIONare then added
2. 2
   ТемператураThe mixture is heated
3. 3
   Температураat reflux for 2 h.
4. 4
   Температураis maintained for 10 minutes
5. 5
   ДругоеAfter filteration through kieselguhr and evaporation of the ether phase the residue
6. 6
   Другоеis purified by flash chromatography on silica (eluent: petroleum ether/ethyl ether 93:7)
7. 7
   workup.DISTILLATIONdistilled in a bulb-tube (Kugelrohr)

Методика

7.9 ml (7.9 mmol) of 1M LiAlH4 solution in ethyl ether and 6 ml of anhydrous ethyl ether are charged under nitrogen into a 25 ml three-necked flask equipped with a thermometer, a condenser and a magnetic stirrer and 3.5 g (15.7 mmol) of (R/S)-2-methyl-4-[(1S,2R,3S,5S)-3-pinanyl]butanal diluted in 6 ml of the same solvent are then added. The mixture is heated at reflux for 2 h. and is then cooled to 10° C. 0.3 ml of water, 0.3 ml of 15% aqueous NaOH solution and 0.8 ml of water are added successively and stirring is maintained for 10 minutes. After filteration through kieselguhr and evaporation of the ether phase the residue is purified by flash chromatography on silica (eluent: petroleum ether/ethyl ether 93:7) and distilled in a bulb-tube (Kugelrohr) to give 2.85 g of (R/S)-2-methyl-4-[(1S,2R,3S,5S)-3-pinanyl]-1-butanol (yield 81%).

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