Acetate → (R)-2-(2,4-difluorophenyl)-3-acetoxy-1,2-propanediol

HRID 356812Notes

Reaction equation

HRID 356812 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:20])([CH2:15][O:16]C(=O)C)[CH2:10][O:11][C:12](=[O:14])[CH3:13].C([O-])(=O)C>C1CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:20])([CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH2:15][OH:16]

Participants

4

Reactant 2

HCID 175AcetateHCID 154634621,3-Diacetoxy-2-(2,4-difluorophenyl)-2-propanol

Product 1

HCID 15463465(R)-2-(2,4-difluorophenyl)-3-acetoxy-1,2-propanediolYield 95.8%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
30 °C

Procedure

A 10 l reaction vessel was charged with 110 g of 2-(2,4-difluorophenyl)-1,3-diacetoxy-2-propanol, 11 g of Lipase made by SEIKAGAKU CORPORATION, (derived from Rhizopus delemar, Enzyme No. 3), 2.8 l of 50 mM acetate buffer (pH 5) and 2.8 l of cyclohexane. The resulting mixture was stirred at 30° C. for 47 hours. The obtained reaction mixture was extracted twice with 3 l of ethyl acetate and the organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 90 g of (R)-2-(2,4-difluorophenyl)-3-acetoxy-1,2-propanediol.

Workup

  1. customA 10 l reaction vessel
  2. customThe obtained reaction mixture
  3. extractionwas extracted twice with 3 l of ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fb981e57545d45ab9cf6d1bde9cd0e5f
Source dataset
uspto-grants-1998_11
Patent number
US05840553

Reaction notes

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