Water → HCID 135848012, compound

HRID 396839Notes

Reaction equation

HRID 396839 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][C:17](=O)[C:18]([F:21])([F:20])[F:19])=[CH:11][C:10]=1[CH2:24][CH3:25])(C(C)(C)C)(C)C.Cl.F[C:28]1[CH:33]=[C:32]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:31]=[CH:30][C:29]=1[NH:38][NH2:39].O.[F-:41].C([N+](CCCC)(CCCC)CCCC)CCC>C(O)C>[CH2:24]([C:10]1[CH:11]=[C:12]([C:15]2[N:38]([C:29]3[CH:30]=[CH:31][C:32]([S:34]([CH3:37])(=[O:36])=[O:35])=[C:33]([F:41])[CH:28]=3)[N:39]=[C:17]([C:18]([F:19])([F:20])[F:21])[CH:16]=2)[CH:13]=[CH:14][C:9]=1[OH:8])[CH3:25]

Participants

6

Reactant 4

HCID 962Water2×HCID 2724141Tetrabutylammonium FluorideHCID 22316849HCID 22316849, compoundHCID 54478909HCID 54478909, compound

Product 1

HCID 135848012HCID 135848012, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(4-[[tert-butyl(dimethyl)silyl]oxy]-3-ethylphenyl)-4,4,4-trifluoro-1,3-butanedione (749 mg, 2.0 mmol) in ethanol (25 ml) was added (2-fluoro-4-methylsulfonylphenyl)hydrazine hydrochloride (530 mg, 2.2 mmol), and the mixture was heated at reflux temperature for 16 hours. The reaction mixture was cooled down to room temperature, and poured into water. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in THF (5 ml). Tetrabutylammonium fluoride (1.0 M solution in THF; 2.5 ml, 2.5 mmol) was added, and the mixture was stirred for 1 hour. Then, the reaction mixture was poured into water. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:2) to give title compound (140 mg, 16% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. extractionThe whole was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in THF (5 ml)
  8. extractionThe whole was extracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography
  13. washeluting with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-1e9331137cb54d5698763c98d8fde73c
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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