Reacción #502075

Ecuación de reacción

water

Sodium hydride

(2S)-6-methylheptan-2-ol

allyl bromide

→

3-{[(1S)-1,5-dimethylhexyl]oxy}prop-1-ene

Rendimiento 66.0%

Disolventes

dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofitted with thermocouple, magnetic stirrer, condenser
2. 2
   Otrorise significantly (41° C. was observed)
3. 3
   workup.STIRRINGThe reaction mixture was stirred for a further 20 minutes until the reaction
4. 4
   Extracciónthe resultant mixture was extracted with methyltert-butyl ether (2×100 mL)
5. 5
   SecadoThe combined organic phase was dried over magnesium sulphate
6. 6
   Otrothe solvent remove in vacuo
7. 7
   Otroto yield a yellow oil which
8. 8
   Otrowas chromatographed over silica gel (hexane/methyltert-butyl ether)

Procedimiento

Sodium hydride (60% dispersion in mineral oil, 2.9 g, 72 mmol) and dimethylformamide (100 mL) were charged to a 250 mL three-necked flask fitted with thermocouple, magnetic stirrer, condenser and dropping funnel. To the reaction mixture was added a solution of (2S)-6-methylheptan-2-ol (3.1 g, 24 mmol) in dimethylformamide (10 mL). This reaction mixture was stirred at room temperature for 1 hr then allyl bromide (8.6 g, 72 mmol) was added dropwise over 10 minutes ensuring the reaction temperature did not rise significantly (41° C. was observed). The reaction mixture was stirred for a further 20 minutes until the reaction was complete. To the reaction mixture was added water (10 mL) and the resultant mixture was extracted with methyltert-butyl ether (2×100 mL). The combined organic phase was dried over magnesium sulphate and the solvent remove in vacuo to yield a yellow oil which was chromatographed over silica gel (hexane/methyltert-butyl ether) to give 3-{[(1S)-1,5-dimethylhexyl]oxy}prop-1-ene as a sl. yellow oil (2.7 g, 15.8 mmol, chemical yield 66%).

Fuente