Reacción #1824337

Ecuación de reacción

Ethyl 5,5-dimethylhexanoate

lithium aluminium hydride

→

5,5-dimethylhexanol

Rendimiento 77.8%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrobefore quenching with 2 ml 15% NaOH and 6 ml water
2. 2
   workup.ADDITIONbefore diluting with dichloromethane
3. 3
   Filtraciónfiltering through CELITE (RTM)
4. 4
   Otrothe solvent evaporated

Procedimiento

Ethyl 5,5-dimethylhexanoate (1.87 g) (prepared in Example 34 with esterification), was dissolved in 30 ml of THF and lithium aluminium hydride (2 g) added portionwise. The reaction was stirred for 2 hours at 0° C. before quenching with 2 ml 15% NaOH and 6 ml water before diluting with dichloromethane and filtering through CELITE (RTM) and the solvent evaporated to give 5,5-dimethylhexanol product (1.1 g) as a slightly volatile liquid. This alcohol was dissolved in 30 ml dichloromethane containing pyridinium chlorochromate and stirred at room temperature to convert it to the corresponding aldehyde, 5,5-dimethylhexanal.

Fuente