Glycerol → HCID 10867504, compound

HRID 1661162Notes

Reaction equation

HRID 1661162 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[CH2:7](N(CC)CC)C.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:14]([O:1][CH2:2][CH:3]1[CH2:5][O:6][CH2:7][O:4]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 753GlycerolHCID 962Water2×HCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 10867504HCID 10867504, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

According to the method of the present invention, 1-(1-benzoyloxymethyl-2-hydroxyethyl)oxymethyl-2-nitroimidazole was produced. That is, 9.2 g of glycerin was dissolved in 100 ml of chloroform, 50 ml of triethylamine was added, and under ice cooling, 14 g of benzoyl chloride was dissolved in 50 ml of chloroform and added dropwise to the above-obtained mixture while stirring. After completion of the dropwise addition, the mixture was returned to room temperature, and stirring was continued for one hour at room temperature. 100 ml of water was added to wash the mixture with water, and then the mixture was concentrated under reduced pressure and purified by silica gel column chromatography (elution solvent; isopropyl ether:methanol 10:0→7:3) (yield; 14.1 g). To 9 g of this product, 100 ml of dimethoxymethane was added, and 1 g of phosphorus pentoxide was slowly added at room temperature while stirring. The mixture was allowed to react continuously for 16 hours. After completion of the reaction, 200 ml of water and 100 ml of ethyl acetate were added thereto, and liquid-liquid extraction was performed. The ethyl acetate layer was dried over sodium sulfate, and then concentrated under reduced pressure. The resultant concentrate was purified by silica gel column chromatography (elution solvent; normal hexane: isopropyl ether 10:0→5:5), to obtain 9.8 g of 4-benzoyloxymethyl-1,3-dioxolane.

Workup

  1. additionadded dropwise to the above-obtained mixture
  2. additionAfter completion of the dropwise addition
  3. customwas returned to room temperature
  4. stirringstirring
  5. washto wash the mixture with water
  6. concentrationthe mixture was concentrated under reduced pressure
  7. custompurified by silica gel column chromatography (elution solvent; isopropyl ether:methanol 10:0→7:3) (yield; 14.1 g)
  8. additionTo 9 g of this product, 100 ml of dimethoxymethane was added
  9. addition1 g of phosphorus pentoxide was slowly added at room temperature
  10. stirringwhile stirring
  11. customto react continuously for 16 hours
  12. additionwere added
  13. extractionliquid-liquid extraction
  14. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  15. concentrationconcentrated under reduced pressure
  16. concentrationThe resultant concentrate
  17. customwas purified by silica gel column chromatography (elution solvent; normal hexane: isopropyl ether 10:0→5:5)

Sources & evidence

ORD record
ord-91d3b17c83634556b62696c3d437ed50
Source dataset
uspto-grants-2011_10
Patent number
US08030338B2

Reaction notes

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