反应详情

A mixture of 6.89 g of tetrahydro-5-[(2-propenyloxy)methyl]-2-furanmethanol (0.04 mole) and 7.12 g of 2-chloro-N,N-dipropylacetamide (0.02 mole) are dissolved in 200 ml of dry dimethyl sulfoxide and the mixture stirred at room temperature under nitrogen. Slowly, 0.50 g of sodium hydride (0.02 mole) is added to the dimethyl sulfoxide mixture and the reaction allowed to stir at ambient temperature (23°). After stirring for 10 minutes an exothermic reaction begins to take place and an ice-bath is used to maintain the reaction temperature below 30°. After stirring for 1 hour, the ice-bath is removed and the reaction allowed to stir at room temperature for 18 hours. The excess NaH is destroyed by adding 5 ml of methanol and the entire reaction mixture is then poured into 400 ml of water. The product is extracted with 3×125 ml portions of chloroform. The CHCl3 extracts are combined and washed with 4×300 ml portions of water. The CHCl3 layer is separated and dried over anhydrous Na2SO4 overnight. The CHCl3 is removed in vacuo yielding a pale yellow oil which is vacuum distilled and the fraction distilling at 185°-188° @ 0.5 mm is collected yielding 8.84 g (70%) of the above compound.

1. stirringto stir at ambient temperature (23°)
2. stirringAfter stirring for 10 minutes
3. customan exothermic reaction
4. temperatureto maintain the reaction temperature below 30°
5. stirringAfter stirring for 1 hour
6. customthe ice-bath is removed
7. stirringto stir at room temperature for 18 hours
8. customThe excess NaH is destroyed
9. additionby adding 5 ml of methanol
10. customthe entire reaction mixture
11. extractionThe product is extracted with 3×125 ml portions of chloroform
12. washwashed with 4×300 ml portions of water
13. customThe CHCl3 layer is separated
14. dry with materialdried over anhydrous Na2SO4 overnight
15. customThe CHCl3 is removed in vacuo
16. customyielding a pale yellow oil which
17. distillationdistilled
18. distillationthe fraction distilling at 185°-188° @ 0.5 mm
19. customis collected