Sodium hydride → 1-[2-Hydroxy-4-(trifluoromethyl)phenyl]ethan-1-one

HRID 858656Notes

Reaction equation

HRID 858656 reaction equation
C([O:3][CH:4]=[CH:5][C:6](=O)[C:7]([F:10])([F:9])[F:8])C.[CH3:12][C:13]([CH2:15][C:16]([CH3:18])=O)=[O:14].[H-].[Na+]>C1COCC1>[OH:3][C:4]1[CH:5]=[C:6]([C:7]([F:8])([F:9])[F:10])[CH:18]=[CH:16][C:15]=1[C:13](=[O:14])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-one

Product 1

HCID 154464491-[2-Hydroxy-4-(trifluoromethyl)phenyl]ethan-1-oneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (5 g, 29.7 mmol) followed by 2,4-pentadione (3.05 ml, 29.7 mmol) were added to a cooled 0° C. suspension of NaH (2.38 g, 59.4 mmol) in THF (120 mL). The reaction mixture was refluxed for 4 hrs and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave the title compound as a yellow oil (1.73 g, 29%). 1H NMR (400 MHz, CDCl3): δ 2.69 (s, 3H), 7.15 (d, J=9.9 Hz, 1 H), 7.25 (s, 1 H), 7.86 (d, J=8.3 Hz, 1 H), 12.29 (s, 1 H).

Workup

  1. additionwere added to a cooled 0° C.
  2. temperatureThe reaction mixture was refluxed for 4 hrs
  3. custompartitioned between 1N HCl and EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a red oil
  7. customPurification by flash column chromatography (0% to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f9bb1708bd8647e29c38359cd6977fd7
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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