Ethanol → HCID 14157591, compound

HRID 1734246Notes

Reaction equation

HRID 1734246 reaction equation
[OH:1][CH2:2][CH:3]1[CH: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][CH:3]1[CH: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 14157574HCID 14157574, compound

Product 1

HCID 14157591HCID 14157591, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(4RS,5SR)-4,5-bis(hydroxymethyl)-1,3-dioxolane obtained in Example 19 was dissolved in 100 ml of pyridine. An excessive amount of acetic anhydride (30.6 g) was added under cooling with ice. After reacting for about four hours at room temperature, 10 ml of ethyl alcohol was added dropwise under cooling with ice to decompose the excessive acetic anhydride. The reaction mixture was concentrated by evaporator. The concentrate was extracted with the addition of 300 ml of ethyl acetate, the extract was washed with water, and the solvent was removed by evaporator. Although it was possible to use this product in the next step as it was, the residue was purified by silica gel column chromatography (eluent, benzene:ethylacetate=95:5) to obtain 18.5 g (yield: 85.0%) of the title compound as a light yellow oil.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. concentrationThe reaction mixture was concentrated by evaporator
  4. extractionThe concentrate was extracted with the addition of 300 ml of ethyl acetate
  5. washthe extract was washed with water
  6. customthe solvent was removed by evaporator
  7. customthe residue was purified by silica gel column chromatography (eluent, benzene:ethylacetate=95:5)

Sources & evidence

ORD record
ord-cfd09eb157384b4b84b71007fecad9ea
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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