Ethanol → HCID 14157593, compound

HRID 1734238Notes

Reaction equation

HRID 1734238 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][OH:9])[O:6][CH2:5][O:4]1.[C:10](OC(=O)C)(=[O:12])[CH3:11].[CH2:17]([OH:19])[CH3:18]>N1C=CC=CC=1>[C:10]([O:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][O:9][C:17](=[O:19])[CH3:18])[O:6][CH2:5][O:4]1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 7918Acetic Anhydride2×HCID 14157576(4R,5R)-1,3-Dioxolane-4,5-dimethanol

Product 1

HCID 14157593HCID 14157593, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The crude (4R,5R)-4,5-bis(hydroxymethyl)-1,3dioxolane obtained in Example 3 was dissolved in 300 ml of pyridine. After the addition of 150 g of excessive amount of acetic anhydride under ice cooling, the mixture was reacted for about 16 hours while stirring at room temperature. 20 ml of ethanol was added in portions while cooling over a water bath in order to decompose the excessive amount of acetic anhydride. After concentration by evaporator, the concentrate was extracted with 500 ml of ethyl acetate and washed with water, followed by removal of the solvent by evaporator. Although this product may be used for the next reaction as it was, the purification by silica gel column chromatography afforded 79.29 g of light yellow oil of (4R,5R)-4,5-bis(acetoxymethyl)-1,3-dioxolane.

Workup

  1. customthe mixture was reacted for about 16 hours
  2. temperaturewhile cooling over a water bath in order
  3. concentrationAfter concentration
  4. customby evaporator
  5. extractionthe concentrate was extracted with 500 ml of ethyl acetate
  6. washwashed with water
  7. customfollowed by removal of the solvent by evaporator
  8. customAlthough this product may be used for the next reaction as it
  9. customthe purification by silica gel column chromatography

Sources & evidence

ORD record
ord-f78425838ddd476ab0034307ac7136b9
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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