反应详情

To 68 ml. of 1.6M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λ max. 2.95 (--OH) and 4.55μ (-C≡C-); vapor phase chromatography shows one peak.

1. additionThe resulting white sludge is diluted with 20 ml
2. custombrought to 10° C.
3. additiontreated with 11 g
4. stirringto stir at ambient temperature for 18 hours
5. customThe organic phase is separated
6. washwashed
7. additionwith dilute hydrochloric solution
8. dry with materialdried with anhydrous magnesium sulfate
9. distillationDistillation
10. customgives 5.1 g