Pyridine → 2-Propanol, 1-(hexadecyloxy)-3-(triphenylmethoxy)-

HRID 2226298Notes

Reaction equation

HRID 2226298 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:21][OH:22])[OH:20])[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][CH3:16].N1C=CC=CC=1.[C:29]1([C:35]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)Cl)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CCOCC>[CH2:1]([O:17][CH2:18][CH:19]([CH2:21][O:22][C:35]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[OH:20])[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][CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6456Trityl chlorideHCID 727331-O-Hexadecylglycerol

Product 1

HCID 4996132-Propanol, 1-(hexadecyloxy)-3-(triphenylmethoxy)-Yield 117.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

rac-1-O-Hexadecylglycerol (1.3 g, 4.17 mmol) and anhydrous pyridine (20 ml) were placed in a flame-dried 50 ml round-bottomed flask flushed with N2. Triphenylchloromethane (2.38 g, 8.54 mmol) was added to the solution and the reaction mixture was stirred for 48 hours. Ice cold H2O and ether were added. The ether layer was removed, washed with H2O, dried (MgSO4), and filtered. The solvent was removed under reduced pressure. Residual pyridine was removed as an azeotrope with toluene. The resulting white solid was dissolved in petroleum ether, and the solution refluxed for one hour to precipitate the triphenylmethanol. The solution was filtered and the petroleum ether removed to yield the crude product 36, rac-1-O-hexadecyl-3-O-tritylglycerol (2.73 g, theoretical yield=2.29 g ). The product was not purified further, but used directly in the next synthesis.

Workup

  1. customflushed with N2
  2. customThe ether layer was removed
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customResidual pyridine was removed as an azeotrope with toluene
  8. dissolutionThe resulting white solid was dissolved in petroleum ether
  9. temperaturethe solution refluxed for one hour
  10. customto precipitate the triphenylmethanol
  11. filtrationThe solution was filtered
  12. customthe petroleum ether removed

Sources & evidence

ORD record
ord-26eb4b683e4f4574a690b2323de6ee8f
Source dataset
uspto-grants-1994_09
Patent number
US05347030

Reaction notes

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