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

HRID 2248043Notes

Reaction equation

HRID 2248043 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 4N 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-7a0d45f5190e455091095123c5862884
Source dataset
uspto-grants-1991_08
Patent number
US05037827

Reaction notes

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