Phenyl chloroformate → 1,3-O-diphenyloxycarbonyl-2-O-methylglycerol

HRID 327493Notes

Reaction equation

HRID 327493 reaction equation
[CH3:1][O:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[C:8](Cl)(=[O:16])[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[OH2:19]>N1C=CC=CC=1>[C:10]1([O:9][C:8]([O:5][CH2:4][CH:3]([CH2:6][O:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:19])[O:2][CH3:1])=[O:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 111709312-Methoxypropane-1,3-diolHCID 21885828Hydrate;hydrochloride

Product 1

HCID 189999891,3-O-diphenyloxycarbonyl-2-O-methylglycerol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20 g of 2-methoxy-1,3-propanediol was dissolved in 200 ml of pyridine. 52.6 ml of phenyl chlorocarbonate was added dropwise to the solution under stirring and under cooling with ice. After two hours, the reaction solution was added to 1 l of 4 N hydrochloric acid/water. After extraction with ether, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, concentrated and purified according to silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 52 g of the intended product.

Workup

  1. temperatureunder cooling with ice
  2. extractionAfter extraction with ether
  3. washthe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-53b6fdec4b8445b29351b09eed813dea
Source dataset
uspto-grants-1993_12
Patent number
US05273985

Reaction notes

Loading…