Glycerol → 3-Trityloxypropane-1,2-diol

HRID 2309296

Reaction equation

HRID 2309296 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:7]([O:1][CH2:2][CH:3]([OH:4])[CH2:5][OH:6])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 753GlycerolHCID 6456Trityl chloride

Product 1

HCID 28828273-Trityloxypropane-1,2-diol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

100 mmol of the glycerol derivative obtained in (b) in 10 ml of pyridine were reacted at room temperature overnight with 101 mmol of trityl chloride. The pyridine was removed under reduced pressure and the residue was taken up in 100 ml of ether. The solution was filtered, the ether was removed and the residue was treated with 10 ml of pyridine, 1 ml of water and 1 g of potassium bicarbonate and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and moisture residues were removed with toluene. The residue was taken up in toluene and chromatographed on silica gel with ether/pyridine (99:1). There was obtained (RS)-1-O-[3RS,7R,11R)-3,7,11,15-tetramethylhexadecyl]-3-O-tritylglycerol as an oil.

Workup

  1. customThe pyridine was removed under reduced pressure
  2. filtrationThe solution was filtered
  3. customthe ether was removed
  4. additionthe residue was treated with 10 ml of pyridine, 1 ml of water and 1 g of potassium bicarbonate
  5. customThe solvent was removed under reduced pressure and moisture residues
  6. customwere removed with toluene
  7. customchromatographed on silica gel with ether/pyridine (99:1)

Sources & evidence

ORD record
ord-82a5eb09337b4f7cbbae81b5fc6c9baa
Source dataset
uspto-grants-1987_09
Patent number
US04694084

Linked notes

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