Trityl chloride → 1-Benzyl-3-tritylglycerol

HRID 2226293Notes

Reaction equation

HRID 2226293 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][OH:13])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][CH:10]([CH2:12][O:13][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 980723-(Benzyloxy)-1,2-propanediol

Product 1

HCID 36083721-Benzyl-3-tritylglycerolYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

rac-1-O-Benzylglycerol (5.37 g, 29.5 mmol), trityl chloride (8.31 g, 29.8 mmol) and anhydrous pyridine (35 ml) were placed in a flame-dried 200 ml round-bottomed flask. The reaction mixture was stirred under anhydrous conditions at room temperature for two days. The precipitate which formed was filtered before H2O and ether were added. The ether layer was extracted with H2O, 1N HCl and H2O, and dried (MgSO4). The solvent was removed by reduced pressure to provide a viscous yellow oil. The crude product was purified by column chromatography (180 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 3:1) to yield pure compound 12, rac-1-O-benzyl-3-O-tritylglycerol (9.00 g, 72% yield).

Workup

  1. customThe precipitate which formed
  2. filtrationwas filtered before H2O and ether
  3. additionwere added
  4. extractionThe ether layer was extracted with H2O, 1N HCl and H2O
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by reduced pressure
  7. customto provide a viscous yellow oil
  8. customThe crude product was purified by column chromatography (180 g silica gel; hexanes:ethyl acetate, gradient 8:1 to 3:1)

Sources & evidence

ORD record
ord-085f3008974143818aaa0a468159ffeb
Source dataset
uspto-grants-1994_09
Patent number
US05347030

Reaction notes

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