反应详情

Methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate (1 eq.) from the previous step and iodomethane (19 eq.) were taken up in THF (0.3 M). To this solution was then added sodium hydride (60% w/w dispersion in oil, 1 eq.) and the resulting suspension was stirred at RT in darkness for 18 h. The volatiles were then removed in vacuo and the resulting residue partitioned between ether and 1 N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) EtOAc:Hex) afforded the title compound as a pale yellow oil.

1. customThe volatiles were then removed in vacuo
2. customthe resulting residue partitioned between ether and 1 N aq. HCl
3. customThe aqueous layer was separated
4. extractionback-extracted with ether
5. washThe combined organic extracts were then washed further with 1 N aq. NaOH, water and brine
6. dry with materialThis was then dried over Na2SO4
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customto afford a yellow oil
10. customPurification of the crude product
11. customthus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) EtOAc:Hex)