Acetic Anhydride → (S)-2-(2,4-difluorophenyl)-1-acetoxy-1,2-propanediol

HRID 1003776

Reaction equation

HRID 1003776 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]O.CC(O)C[CH2:18][CH:19]([OH:21])C.C(OC(=O)C)(=[O:25])C>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:14])([CH3:10])[C@H:12]([O:13][C:19](=[O:21])[CH3:18])[OH:25]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 180492,5-HexanediolHCID 112179522-(2,4-Difluorophenyl)-1,2,3-propanetriol

Product 1

HCID 53684152(S)-2-(2,4-difluorophenyl)-1-acetoxy-1,2-propanediol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A 300 ml reaction vessel was charged with 5 g of 2-(2,4-difluorophenyl)-1,2,3-propanetriol, 100 ml of diisopropanol, 2.45 ml of acetic anhydride and 5 g of Novozym 435 made by NOVO NORDISK, Ltd (derived from Candida antarctica, Enzyme No. 24). The resulting mixture was stirred at 30° C. for 15 hours. After 10 ml of water was added thereto, the reaction liquid was filtered to remove the enzyme. An organic layer of the filtrate was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give 1 g of (S)-2-(2,4-difluorophenyl)-1-acetoxy-1,2-propanediol. The optical purity thereof was 8% ee.

Workup

  1. customA 300 ml reaction vessel
  2. customthe reaction liquid
  3. filtrationwas filtered
  4. customto remove the enzyme
  5. dry with materialAn organic layer of the filtrate was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-6030b8f3be1e4bb5b701813f077b0c10
Source dataset
uspto-grants-2000_04
Patent number
US06046354

Linked notes

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