反应详情

0.7 g of 60% sodium hydride in mineral oil was added to 25 ml of dry 1,2-dimethoxyethane. The contents were stirred, and 2.5 g (0.010 moles) of 6-benzyloxy-2napthol was slowly added. After stirring the resulting solution for 20 minutes at room temperature, it was cooled with an ice bath. 4.1 g (0.011 moles) of 5-ethoxy-2,2,3,3,4,4-hexafluoropentyl trifluoromethanesulfonate (prepared essentially as in Example 3) was then added slowly. When this addition was complete, the ice bath was removed, and the product-containing mixture was stirred overnight at room temperature. The solvent was then removed under reduced pressure, and 30 ml of water, followed by 30 ml of diethyl ether, were added sequentially. Once all of the solids had dissolved, two homogeneous liquid layers formed. The layers were separated, and the aqueous layer was extracted twice with 25 ml aliquots of diethyl ether. The resulting ether layers were combined, washed three times with 20 ml aliquots of deionized water, dried with anhydrous magnesium sulfate, and stripped to dryness using a rotary evaporator. The resulting solid was dissolved in tetrahydrofuran and was hydrogenated at 60 psi in the presence of catalytic 10% palladium on carbon for 18 hours. When the hydrogenation was complete, the catalyst was removed by filtration, and the solvent was removed on a rotary evaporator. The resulting brown semisolid material was then purified by using chromatography on silica gel (2.5% methanol in chloroform) to yield 1.64 g of 6-(5-ethoxy-2,2,3,3,4,4-hexafluoropentoxy)-2-hydroxynapthalene product.

1. stirringAfter stirring the resulting solution for 20 minutes at room temperature
2. temperatureit was cooled with an ice bath
3. additionwas then added slowly
4. additionWhen this addition
5. customthe ice bath was removed
6. stirringthe product-containing mixture was stirred overnight at room temperature
7. customThe solvent was then removed under reduced pressure, and 30 ml of water
8. additionwere added sequentially
9. dissolutionOnce all of the solids had dissolved
10. customtwo homogeneous liquid layers formed
11. customThe layers were separated
12. extractionthe aqueous layer was extracted twice with 25 ml aliquots of diethyl ether
13. washwashed three times with 20 ml aliquots of deionized water
14. dry with materialdried with anhydrous magnesium sulfate
15. customa rotary evaporator
16. dissolutionThe resulting solid was dissolved in tetrahydrofuran
17. customthe catalyst was removed by filtration
18. customthe solvent was removed on a rotary evaporator
19. customThe resulting brown semisolid material was then purified