참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Batyl Alcohol | HCID 3681 | — |
| 반응물 | Trityl chloride | HCID 6456 | — |
| 반응물 | Triethylamine | HCID 8471 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 생성물 | 1-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol | HCID 12896848 | 93.7% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US05730157 |
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| 출처 데이터셋 | uspto-grants-1998_03 |
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| ORD ID | ord-0332df00e2284765af8a85ebe5acb072 |
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| 출처 메모 | uspto-grants-1998_03 |
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