Acetic Anhydride → 1,3-Diacetoxy-2-(2,4-difluorophenyl)-2-propanol

HRID 1003765Notes

Reaction equation

HRID 1003765 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:14])([CH2:12][OH:13])[CH2:10][OH:11].[C:15](OC(=O)C)(=[O:17])[CH3:16].[C:22](OCC)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:15]([O:11][CH2:10][C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([OH:14])[CH2:12][O:13][C:22](=[O:24])[CH3:23])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 112179522-(2,4-Difluorophenyl)-1,2,3-propanetriol

Product 1

HCID 154634621,3-Diacetoxy-2-(2,4-difluorophenyl)-2-propanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 100 ml of pyridine was dissolved 10 g of 2-(2,4-difluorophenyl)-1,2,3-propanetriol. To the resulting solution was added dropwise 1.1 g of acetic anhydride at room temperature. After the dropping, the resulting liquid was stirred at room temperature for 1 hour. Then, to the reaction mixture was added 50 ml of ethyl acetate, and an organic layer was separated therefrom. After the organic layer was washed with 1N aqueous solution of hydrochloric acid and further washed with water and saturated aqueous solution with sodium chloride. Then the organic layer was dried over anhydrous sodium sulfate. The resulting organic layer was filtered and the solvent was removed under reduced pressure. Thus obtained concentrate was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 12.5 g of the desired compound.

Workup

  1. customan organic layer was separated
  2. washAfter the organic layer was washed with 1N aqueous solution of hydrochloric acid
  3. washfurther washed with water and saturated aqueous solution with sodium chloride
  4. dry with materialThen the organic layer was dried over anhydrous sodium sulfate
  5. filtrationThe resulting organic layer was filtered
  6. customthe solvent was removed under reduced pressure
  7. customThus obtained
  8. concentrationconcentrate
  9. customwas purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-21d4e998dbbf4a1da335593bc4d26aa2
Source dataset
uspto-grants-2000_04
Patent number
US06046354

Reaction notes

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