Hydrochloric Acid → 4,4,4-Trifluoro-1-[4-(2-furyl)-2-methylphenyl]butane-1,3-dione

HRID 497211Notes

Reaction equation

HRID 497211 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[C:20]([CH3:27])[CH:19]=1.Cl>C(OC)(C)(C)C>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:25][C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:14]2[O:13][CH:17]=[CH:16][CH:15]=2)=[CH:19][C:20]=1[CH3:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 223166271-[4-(2-Furyl)-2-methylphenyl]ethanone

Product 1

HCID 223168124,4,4-Trifluoro-1-[4-(2-furyl)-2-methylphenyl]butane-1,3-dioneYield 104.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a stirred solution of ethyl trifluoroacetate (9.90 g, 6.31 mmol) in t-butylmethylether (3 ml) was added sodium methoxide (28 wt. % solution in methanol, 1.5 ml, 6.23 mmol) over 2 min. A solution of 1-[4-(2-furyl)-2-methylphenyl]ethanone (1.15 g. 5.74 mmol) in t-butylmethylether (4 ml) was added dropwise over 5 min. and the mixture was stirred for 20 hours. 2N HCl (10 ml) was added, and the whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give 1.78 g of brown oil. The compound was used for next reaction without purification.

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ab2de35e4c734a5a843b5f05428bfca9
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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