反应详情

温度

0 °C

The ethylhexadecadienoate was reduced with lithium aluminum hydride (LAH) in tetrahydrofuran as follows. An oven dried 3-neck flask equipped with a magnetic stirrer, reflux condenser and an addition funnel was charged with 2 equivalents of LAH in dry tetrahydrofuran (THF). The reaction vessel and contents were maintained under a positive flow of nitrogen as 1 equivalent of ester (ethylhexadecadienoate) dissolved in an equal volume of dry THF was added dropwise to the stirred LAH suspension at a rate to maintain the THF at a gentle boil. After ester addition was complete, the reaction mixture was refluxed gently for an additional 2 hours, cooled to 0° C. and one equivalent of water slowly added to decompose excess LAH, followed by addition of 15% aqueous NaOH. The resulting gray gel was filtered and the organic layer washed with water, dried over adsorbent and concentrated on a rotary evaporator. Yields of about 41% of the desired 7,11-hexadecadien-1-ol were obtained.

1. customAn oven dried 3-neck flask
2. customequipped with a magnetic stirrer
3. temperaturereflux condenser and an addition funnel
4. temperaturethe reaction mixture was refluxed gently for an additional 2 hours
5. filtrationThe resulting gray gel was filtered
6. washthe organic layer washed with water
7. customdried over adsorbent and
8. concentrationconcentrated on a rotary evaporator