Trityl chloride → HCID 69748255, compound

HRID 1530858Notes

Reaction equation

HRID 1530858 reaction equation
[OH:1][CH:2]([CH2:24][OH:25])[CH2:3][O:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:26]1([C:32](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl.N1C=CC=CC=1>[OH:1][CH:2]([CH2:24][O:25][C:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:3][O:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 5283468Glyceryl Monooleate

Product 1

HCID 69748255HCID 69748255, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

A solution of 2 (21 mmol) in 80 ml of dichloromethane/pyridine (1:1) is added dropwise with triphenylmethyl chloride (27 mmol) and stirred at room temperature for 48 hours. The solvent is removed, and the residue is added twice with 50 ml of toluene and concentrated. The residue is diluted with 100 ml of H2O and extracted three times with 50 ml of dichloromethane. The combined organic phases are washed with 50 ml of cold 5% HCl and 50 ml of saturated NaCl solution, dried over MgSO4, filtrated and concentrated. The residue is purified by chromatography on silica gel using heptane/ethyl acetate (5:1). Yield: 88% of a colorless oil.

Workup

  1. customThe solvent is removed
  2. additionthe residue is added twice with 50 ml of toluene
  3. concentrationconcentrated
  4. additionThe residue is diluted with 100 ml of H2O
  5. extractionextracted three times with 50 ml of dichloromethane
  6. washThe combined organic phases are washed with 50 ml of cold 5% HCl and 50 ml of saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltrated
  9. concentrationconcentrated
  10. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-50e417f217424b1da3b46e06677be099
Source dataset
uspto-grants-2001_03
Patent number
US06197759B1

Reaction notes

Loading…