Ethyl trifluoroacetate → 1-[4-(Benzyloxy)phenyl]-4,4,4-trifluorobutane-1,3-dione

HRID 1366365Notes

Reaction equation

HRID 1366365 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([C:22](OCC)=[O:23])([F:21])([F:20])[F:19].CC[O-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH2:16][C:22](=[O:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-oneHCID 2723922Sodium ethoxide

Product 1

HCID 218944541-[4-(Benzyloxy)phenyl]-4,4,4-trifluorobutane-1,3-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

45.2 g 1-(4-Benzyloxy-phenyl)ethanone (200 mmol) was taken up in THF (250 mL) and treated with CF3CO2Et (30 ml, 250 mmol). The solution was cooled to 0° C. and treated with 2.66 M NaOEt (94 ml, 250 mmol) solution over 1 h. The ice bath was removed and the solution was stirred at room temperature for 4 h. The reaction was poured into 1 N HCl (1000 ml) and extracted with EtOAc (1500 ml). The organic layer was washed with brine, dried and evaporated to yield 64.2 g 1-(4-Benzyloxy-phenyl)-4,4,4-trifluoro-butane-1,3-dione (200 mmol, 100% yield).

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was poured into 1 N HCl (1000 ml)
  3. extractionextracted with EtOAc (1500 ml)
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-426af1ae24374c0eb56015b80d306be0
Source dataset
uspto-grants-2011_02
Patent number
US07893057B2

Reaction notes

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