반응 #54559

반응 방정식

2-dimethylaminoethyl chloride

2,2-dimethyl-4-(1-naphthyl)-7-chromanol

sodium hydride

→

oil

수율 67.2%

2,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-(1-naphthyl)chroman

수율 67.2%

용매

toluene

water

toluene

반응 조건

후처리

1. 1
   온도to reflux
2. 2
   온도under reflux for 2 hours
3. 3
   온도cooled
4. 4
   workup.WAITleft
5. 5
   기타Next day the toluene layer was separated
6. 6
   기타evaporated in vacuo
7. 7
   추출The aqueous layer was extracted with ether
8. 8
   workup.DISSOLUTIONto dissolve the residue
9. 9
   기타from the toluene evaporation
10. 10
    추출The organic layer was extracted with 5 N hydrochloric acid (45, 35 and 20 ml respectively), the combined acid
11. 11
    추출extract
12. 12
    추출extracted into ether
13. 13
    건조After being dried the ether
14. 14
    기타was removed in vacuo

실험 절차

To a stirred solution of 2,2-dimethyl-4-(1-naphthyl)-7-chromanol (7.48 g) in dry toluene (50 ml) was added sodium hydride (1.5 g, ~1.5 eq., 60% dispersion in oil) and the mixture was brought to reflux. To the resulting solution was added dropwise over 10 minutes a solution of 2-dimethylaminoethyl chloride (2.70 g, ~1.1 eq.) in dry toluene (10 ml) and the mixture was stirred under reflux for 2 hours, cooled, diluted with water and left to stand overnight. Next day the toluene layer was separated and evaporated in vacuo. The aqueous layer was extracted with ether and the extract used to dissolve the residue from the toluene evaporation. The organic layer was extracted with 5 N hydrochloric acid (45, 35 and 20 ml respectively), the combined acid extract was basified and extracted into ether. After being dried the ether was removed in vacuo to give a yellow oil (6.2 g) which was chromatographed on alumina in 8% ether--92 % petroleum ether (b.p. 60-80) to give the title compound (4.71 g, 51%) as a colourless oil. The hydrochloric salt had m.p. 178.5°-181.5° C.

출처