Methyl iodide → 1-o-Oleyl-2-o-methyl-3-o-trityl glycerol

HRID 496993

반응식

HRID 496993 반응식
[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][OH:24])[OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[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.[H-].[Na+].[CH3:47]I>N1C=CC=CC=1.C1COCC1.O>[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][C:25]([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)[O:22][CH3:47])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 5282282Selachyl alcohol

생성물 1

HCID 694707801-o-Oleyl-2-o-methyl-3-o-trityl glycerol

시약·촉매·용매 3

HCID 962Water용매HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

Diol Compound 20 (2.0 g, 5.97 mmol) was added dropwise to a solution of trityl chloride (1.66 g, 6.0 mmol) in anhydrous pyridine (10 mL). The reaction was left to stir for 16 hours after which the solvent was removed by co-evaporation with toluene (2×5 mL). Then, part of the residue (1.0 g, 1.7 mmol) was added dropwise to a suspension of NaH (0.14 g, 3.4 mmol) in THF (50 mL), followed by the addition of MeI (0.22 mL, 3.4 mmol). After 16 hours, TLC analysis showed that the reaction had gone to completion and H2O (5 mL) was added followed by concentration of the reaction mixture. The residue was partitioned between H2O (20 mL) and diethyl ether (100 mL), the organic extract was washed with sat. NaHCO3 (10 mL), dried (MgSO4) and concentrated to give 1-O-oleyl-2-O-methyl-3-O-trityl glycerol (Cornpound 21) as an oil.

후처리

  1. waitThe reaction was left
  2. customwas removed by co-evaporation with toluene (2×5 mL)
  3. waitAfter 16 hours
  4. additionwas added
  5. customThe residue was partitioned between H2O (20 mL) and diethyl ether (100 mL)
  6. extractionthe organic extract
  7. washwas washed with sat. NaHCO3 (10 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9a7a7b355b1a46eda5505c7a3f3adb6b
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949529B2

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