反应详情

Benzene (250 ml) was added to 95% sodium hydride (11.4 g, 450.0 mmol), and the flask was flushed with nitrogen and sealed. A solution of 3-allyloxy-1,2-propanediol (6.6 g, 50.0 mmol) in benzene (75 ml) was added to the flask. Using a syringe, 97% 1-bromotetradecane (36.7 ml, 120.0 mmol) was added to the flask and the reaction was left to reflux overnight under a constant stream of nitrogen. Once cooled to room temperature, the excess sodium hydride was slowly quenched with ethanol until no further effervescence was observed. The solution was transferred to a separatory funnel with benzene (250 ml) and washed with distilled water (3×200 ml). The organic layer was dried with magnesium sulfate and the solvent removed on the rotary evaporator to yield a colourless oil. TLC (5% ether-hexane, developed in Molybdate) indicated that most of the starting material had reacted to form product. This resulting product was further purified by flash column chromatography (1-5% ether-hexane) to yield 15.0 g (57.3%) of 1,2-dimyristyloxy-3-allyloxypropane 1.

1. customthe flask was flushed with nitrogen
2. customsealed
3. waitthe reaction was left
4. temperatureto reflux overnight under a constant stream of nitrogen
5. customthe excess sodium hydride was slowly quenched with ethanol until no further effervescence
6. customThe solution was transferred to a separatory funnel with benzene (250 ml)
7. washwashed with distilled water (3×200 ml)
8. dry with materialThe organic layer was dried with magnesium sulfate
9. customthe solvent removed on the rotary evaporator
10. customto yield a colourless oil
11. customhad reacted
12. customto form product
13. customThis resulting product was further purified by flash column chromatography (1-5% ether-hexane)