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

HRID 496993

Reaction equation

HRID 496993 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9a7a7b355b1a46eda5505c7a3f3adb6b
Source dataset
uspto-grants-2005_09
Patent number
US06949529B2

Linked notes

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