Sodium hydride → 2-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-4-methyl-pentane-1,3-dione

HRID 14459Notes

Reaction equation

HRID 14459 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[C:18]([O:19]C(=O)C(C)C)=[C:17]([F:25])[C:16]([F:26])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1>O1CCCC1.Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:11](=[O:12])[CH:13]([CH3:18])[CH3:14])[C:11]([C:13]2[CH:14]=[CH:15][C:16]([F:26])=[C:17]([F:25])[C:18]=2[OH:19])=[O:12])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 68703339Isobutyric acid 6-[2-(4-chlorophenyl)acetyl]-2,3-difluorophenyl ester

Product 1

HCID 686997002-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-4-methyl-pentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (1.5 g, 37.5 mmol, 60% dispersion in mineral oil, 4 eq.) is added portionwise to a stirred solution of isobutyric acid 6-[2-(4-chlorophenyl)acetyl]-2,3-difluorophenyl ester (3.16 g, 8.97 mmol) in tetrahydrofuran (60 ml) over 15 min. The mixture is heated in an oil bath at 80° C. for 4 h. The reaction is cooled to room temperature, diluted with 2M HCl solution and washed with ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound as a brown oil. The product is used in the next step without further purification.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. washwashed with ethyl acetate
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23a03a55e48c4fb1add8abb696fa5369
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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