Hydrochloric Acid → Methyl {3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

HRID 660901ノート

反応式

HRID 660901 の反応式
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:27][O:28][C:29](=[O:47])[CH2:30][N:31]1[C:35](=[O:36])[N:34]([CH2:37][CH:38]=[O:39])[C:33]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)=[N:32]1.Cl>C1COCC1>[CH3:27][O:28][C:29](=[O:47])[CH2:30][N:31]1[C:35](=[O:36])[N:34]([CH2:37][CH:38]([OH:39])[C:2]([F:4])([F:3])[F:1])[C:33]([C:40]2[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=2)=[N:32]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 58011652Methyl [3-(4-chlorophenyl)-4-(2-oxoethyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

生成物 1

HCID 58011736Methyl {3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒4 回

実験手順

6.69 ml of a 0.5 M solution of (trifluoromethyl)trimethylsilane in THF (3.34 mmol) and 39 μl of a 1 M solution of tetra-n-butylammonium fluoride in THF (39 μmol) are successively added at 0° C. to a solution of 948 mg (2.57 mmol) of the compound from Example 225A in 17 ml THF. The temperature is allowed to rise to RT and the mixture stirred for 1 hr more. For the workup, the reaction mixture is treated with 8 ml of 1 N hydrochloric acid. It is stirred for 1 hr at RT, before the THF is removed on the rotary evaporator. The aqueous residue is extracted with ethyl acetate. The organic phase is washed twice with water and once with sat. sodium chloride solution, dried over magnesium sulphate and freed of solvent on the rotary evaporator. The residue is purified by silica gel chromatography (eluent: dichloromethane/methanol 100:1→100:2). 630 mg (65% of theory) of the title compound are obtained.

後処理

  1. customto rise to RT
  2. customis removed on the rotary evaporator
  3. extractionThe aqueous residue is extracted with ethyl acetate
  4. washThe organic phase is washed twice with water and once with sat. sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customfreed of solvent on the rotary evaporator
  7. customThe residue is purified by silica gel chromatography (eluent: dichloromethane/methanol 100:1→100:2)

出典と根拠

ORDレコード
ord-b3f0ca5a743e43c79b02fe9ccb55804b
出典データセット
uspto-grants-2011_12
特許番号
US08084481B2

反応ノート

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