Batyl Alcohol → 1-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol

HRID 1377451

反応式

HRID 1377451 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23].[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:18]([O:19][CH2:20][CH:21]([CH2:22][O:23][C:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[OH:24])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

参加物

5

反応物 3

HCID 3681Batyl AlcoholHCID 6456Trityl chloride2 回HCID 8471Triethylamine

生成物 1

HCID 128968481-(Octadecyloxy)-3-(triphenylmethoxy)propan-2-ol収率 93.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

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.

後処理

  1. custombe freshly recrystallized from halpasol, trademark for a petroleum ether fraction, b.p. 100°-120° C.)
  2. temperature(cooling with a water bath)
  3. waitThe reaction is continued for six hours at ambient temperature
  4. washThe solution is then washed with 300 ml of a NaHCO3 solution (1%)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. dissolutionThe oily residue (155 g) is dissolved in 660 ml acetonitrile
  9. temperatureAfter cooling to room temperature the title product
  10. customcrystallizes (preferentially
  11. additionafter adding a few seed crystals)
  12. customCrystallization
  13. waitby standing overnight at ambient temperature
  14. filtrationThe crystallizate is filtered off

出典と根拠

ORDレコード
ord-0794b48209a7458dbdb5636a6e327fa3
出典データセット
uspto-grants-1997_09
特許番号
US05665714

関連ノート

読み込み中…