反応 #2725

反応方程式

triethylamine

batylalcohol

tritylchloride

tritylchloride

→

crude product

収率 93.7%

1-O-n-Octadecyl-3-O-Trityl-Glycerol

収率 93.7%

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他be freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.)
2. 2
   温度(cooling with a water bath)
3. 3
   workup.WAITThe reaction is continued for six hours at ambient temperature
4. 4
   洗浄The solution is then washed with 300 ml of a NaHCO3 solution (1%)
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   ろ過filtered
7. 7
   その他evaporated under vacuum
8. 8
   workup.DISSOLUTIONThe oily residue (155 g) is dissolved in 660 ml acetonitrile
9. 9
   温度After cooling to room temperature the title product
10. 10
    その他crystallizes (preferentially
11. 11
    workup.ADDITIONafter adding a few seed crystals)
12. 12
    その他Crystallization
13. 13
    workup.WAITby standing overnight at ambient temperature
14. 14
    ろ過The crystallizate is filtered off

実験手順

51.69 Grams (150 mmol) of batylalcohol and 62.73 g (225 mmol) freshly recrystallized tritylchloride are dissolved at 35° C. in 350 ml methylene chloride. (Note: It is recommended that the tritylchloride be freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.). During 15 minutes, 22.77 g (225 mmol; 31.38 ml) triethylamine is added dropwise to the stirred solution at 30°-35° C. (cooling with a water bath). The reaction is continued for six hours at ambient temperature. (Note: It is recommended that a control TLC be done to make sure that the reaction is complete). The solution is then washed with 300 ml of a NaHCO3 solution (1%), dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The oily residue (155 g) is dissolved in 660 ml acetonitrile by warming up to 70° C. with stirring. After cooling to room temperature the title product crystallizes (preferentially after adding a few seed crystals). Crystallization is completed by standing overnight at ambient temperature. The crystallizate is filtered off to yield 82.5 g (93.7%) of crude product (m.p. 53°-55° C.) which can be used for the following step without purification. Recrystallization from halpasol (310 ml) yields 71 g (80%) of pure tritylbatylalcohol. B. In a similar way, introduction of the 3-O-trityl function is accomplished for each 1-O-R-glycerol of Example 2-B.

出典