Ethanol → HCID 14157594, compound

HRID 1734243Notes

Reaction equation

HRID 1734243 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][C@H:9]1[C@H:13]([CH2:14][OH:15])[O:12][CH2:11][O:10]1.[C:16](OC(=O)C)(=[O:18])[CH3:17].[CH2:23]([OH:25])[CH3:24]>>[C:16]([O:7][CH2:8][C@H:9]1[C@H:13]([CH2:14][O:15][C:23](=[O:25])[CH3:24])[O:12][CH2:11][O:10]1)(=[O:18])[CH3:17]

Participants

5

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 7918Acetic Anhydride2×HCID 14157577HCID 14157577, compound

Product 1

HCID 14157594HCID 14157594, compound

Procedure

200 ml of pyridine was added to crude (4S,5S)-4,5-bis(hydroxymethyl)-1,3-dioxolane obtained in Example 14 to dissolve the latter. An excessive amount of acetic anhydride (200 g) was added dropwise under cooling with ice. After several hours of reaction, ethyl alcohol was added dropwise to decompose the excessive acetic anhydride. The reaction mixture was concentrated by evaporator to remove almost all pyridine. The concentrate was extracted with the addition of 500 ml of ethyl acetate. The extract was washed with saturated aqueous solution of sodium hydrogen carbonate, then with water, dried, and concentrated by evaporator. The residue was purified by silica gel column chromatography (eluent, benzene:ethylacetate=9:1) to obtain 90.0 g of the title compound as a colorless liquid.

Workup

  1. dissolutionto dissolve the latter
  2. temperatureunder cooling with ice
  3. additionwas added dropwise
  4. concentrationThe reaction mixture was concentrated by evaporator
  5. customto remove almost all pyridine
  6. extractionThe concentrate was extracted with the addition of 500 ml of ethyl acetate
  7. washThe extract was washed with saturated aqueous solution of sodium hydrogen carbonate
  8. dry with materialwith water, dried
  9. concentrationconcentrated by evaporator
  10. customThe residue was purified by silica gel column chromatography (eluent, benzene:ethylacetate=9:1)

Sources & evidence

ORD record
ord-58024ed68a87487cad194f9d741ff1ad
Source dataset
uspto-grants-1996_07
Patent number
US05532380

Reaction notes

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