تفاعل #2725

معادلة التفاعل

triethylamine

batylalcohol

tritylchloride

tritylchloride

→

crude product

المردود 93.7%

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

المردود 93.7%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىbe freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.)
2. 2
   درجة الحرارة(cooling with a water bath)
3. 3
   workup.WAITThe reaction is continued for six hours at ambient temperature
4. 4
   غسيلThe solution is then washed with 300 ml of a NaHCO3 solution (1%)
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated under vacuum
8. 8
   workup.DISSOLUTIONThe oily residue (155 g) is dissolved in 660 ml acetonitrile
9. 9
   درجة الحرارةAfter cooling to room temperature the title product
10. 10
    أخرىcrystallizes (preferentially
11. 11
    workup.ADDITIONafter adding a few seed crystals)
12. 12
    أخرىCrystallization
13. 13
    workup.WAITby standing overnight at ambient temperature
14. 14
    ترشيحThe crystallizate is filtered off

الإجراء التجريبي

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.

المصدر