反应详情

温度

60 °C

A 3-L 4-neck flask equipped with an overhead stirrer, a thermocouple, a condenser, a nitrogen inlet, and a 1-L addition funnel was charged with potassium (30 g, 0.764 mol) and THF (1 L). The metal suspension was heated to 60° C. for 30 min and then stirred to room temperature. To the reaction mixture was then added naphthalene (2 g, 0.015 mol), the suspension was stirred at room temperature for 10 min and then cooled to −20° C. to afford a blue suspension. A solution of 1H,3H-Benzo[de]isochromene (26 g, 0.153 mol) in THF (500 ml) was slowly added via the addition funnel, with addition controlled so that the reaction temperature did not exceed −15° C. After stirring for 5 h at −20° C., the suspension was removed from the cooling bath, warmed with stirring to 0° C., and then allowed to stand without stirring (potassium metal settling). The solution was decanted and the residual potassium was cooled and carefully decomposed with isopropyl alcohol (IPA) under N2. The decanted solution was carefully treated with water (20 mL) under nitrogen and stirring was continued for 20 min. Additional water and ether were added and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 and the combined organics were dried over MgSO4 and condensed in vacuo to yield a crude material. The crude material was purified by flash chromatography (7.5/2.5 hexane/EtOAc) to yield 8-methyl-1-napthalenemethanol as a solid.

1. customA 3-L 4-neck flask equipped with an overhead stirrer
2. temperaturecooled to −20° C.
3. customto afford a blue suspension
4. customdid not exceed −15° C
5. stirringAfter stirring for 5 h at −20° C.
6. customthe suspension was removed from the cooling bath
7. temperaturewarmed
8. stirringwith stirring to 0° C.
9. stirringwithout stirring (potassium metal settling)
10. customThe solution was decanted
11. temperaturethe residual potassium was cooled
12. additionThe decanted solution was carefully treated with water (20 mL) under nitrogen
13. stirringstirring
14. additionAdditional water and ether were added
15. customthe organic layer was separated
16. extractionThe aqueous layer was extracted with CH2Cl2
17. dry with materialthe combined organics were dried over MgSO4 and condensed in vacuo
18. customto yield a crude material
19. customThe crude material was purified by flash chromatography (7.5/2.5 hexane/EtOAc)