t-Butyl2-acetyl-4-(4-ethylphenyl)-3-oxobutyrate → HCID 178436306, compound

HRID 1625855Notes

Reaction equation

HRID 1625855 reaction equation
[C:1]([CH:4]([C:12](=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=1)C(OC(C)(C)C)=O)(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[CH2:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:12](=[O:22])[CH:4]=[C:1]([OH:3])[CH3:2])=[CH:15][CH:16]=1)[CH3:21]

Participants

3

Reactant 1

HCID 66608203t-Butyl2-acetyl-4-(4-ethylphenyl)-3-oxobutyrate

Product 1

HCID 178436306HCID 178436306, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the above t-butyl 2-acetyl-4-(4-ethylphenyl)-3-oxobutyrate in trifluoroacetic acid (60 ml) was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate, and the mixture was washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine. The mixture was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give 1-(4-ethylphenyl)-4-hydroxy-3-penten-2-one (4.00 g) as yellow oil. APCI-Mass m/Z 205 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe mixture was washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialThe mixture was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aaff97ec30a2469280c559d3cfe4425b
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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