rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol → 1-O-benzyl-2-O-methylglycerol

HRID 2226295Notes

Reaction equation

HRID 2226295 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][O:14]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O>[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][OH:14])[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 14584166rac-1-O-benzyl-2-O-methyl-3-O-tritylglycerol

Product 1

HCID 1294271-O-benzyl-2-O-methylglycerol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

rac-1-O-Benzyl-2-O-methyl-3-O-tritylglycerol (6.73 g) and 80% HOAc (50 ml) were combined in a 100 ml flask and heated at reflux for three hours. The heat was removed and the reaction mixture was allowed to cool to room temperature. The reaction was neutralized with 10% KOH and extracted with ether. The ether layer was dried (MgSO4) before the solvent was removed in vacuo. Purification of the residue was obtained by column chromatography (150 ml silica gel; hexanes:ethyl acetate, gradient 5:1-0:1). The pure compound 14, rac-1-O-benzyl-2-O-methylglycerol, was obtained as a clear oil (1.84 g, 59.7% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for three hours
  3. customThe heat was removed
  4. extractionextracted with ether
  5. dry with materialThe ether layer was dried (MgSO4) before the solvent
  6. customwas removed in vacuo
  7. customPurification of the residue
  8. customwas obtained by column chromatography (150 ml silica gel; hexanes:ethyl acetate, gradient 5:1-0:1)

Sources & evidence

ORD record
ord-c6c912d729c64b38a09f2d7837a9c2fe
Source dataset
uspto-grants-1994_09
Patent number
US05347030

Reaction notes

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