反応 #1281746

反応方程式

Butyl sulfide

methyl butyl sulfide

butanethiol

NaH

6-(6-methoxy-2-naphthyl)-6-oxo-hexanoic acid

→

title compound

収率 79.0%

6-(6-Hydroxy-2-naphthyl)-6-oxohexanoic acid

収率 79.0%

溶媒

water

DMF

DMF

DMF

反応条件

後処理

1. 1
   温度the reaction heated
2. 2
   温度at reflux
3. 3
   温度heated
4. 4
   温度at reflux for 1 hour
5. 5
   workup.DISTILLATIONdistilled (7 torr, 28° C.)
6. 6
   その他to leave a bright yellow powder that
7. 7
   その他precipitated with 5% HCl
8. 8
   ろ過The precipitate was filtered
9. 9
   workup.DISSOLUTIONdissolved in ethyl acetate (1800 ml)
10. 10
    乾燥dried (Na2SO4)
11. 11
    ろ過filtered
12. 12
    その他evaporated
13. 13
    その他to give a yellow solid
14. 14
    その他that was recrystallized (ethyl acetate)

実験手順

Butyl sulfide was generated by placing NaH (2.57 g, 0.11 mol) in a 500 ml round bottom flask, adding butanethiol (5.14 ml, 0.48 mol) and stirring for 5 minutes. DMF (200 mls) was added and the reaction heated at reflux. Slowly, 6-(6-methoxy-2-naphthyl)-6-oxo-hexanoic acid (Example 5) (7.2 g, 0.25 mol) in DMF (100 ml) was added to the reaction and heated at reflux for 1 hour. The methyl butyl sulfide and DMF were vacuum distilled (7 torr, 28° C.) to leave a bright yellow powder that was dissolved in water and precipitated with 5% HCl. The precipitate was filtered, dissolved in ethyl acetate (1800 ml), dried (Na2SO4), filtered and evaporated to give a yellow solid that was recrystallized (ethyl acetate) to give the title compound (5.38 grams, 79% yield), mp 191°-193° C.; MS, m/e 272 (M+).

出典