2,2,3,3-Tetrafluoro-1-propanol → 2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxy-6-(2,2,3,3-tetrafluoropropyloxy)pyridine

HRID 23321

反応式

HRID 23321 の反応式
[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][OH:4].[H-].[Na+].[CH3:11][N:12]1[C:16]([O:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20](OC3N(C)N=C(C(F)(F)F)C=3)[N:19]=2)=[CH:15][C:14]([C:37]([F:40])([F:39])[F:38])=[N:13]1>S1(CCCC1)(=O)=O.CCCCC.C(OCC)(=O)C>[CH3:11][N:12]1[C:16]([O:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:4][CH2:3][C:2]([F:8])([F:1])[CH:5]([F:7])[F:6])[N:19]=2)=[CH:15][C:14]([C:37]([F:40])([F:39])[F:38])=[N:13]1

参加物

6

反応物 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 24758Sodium hydrideHCID 225726302,6-Bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine

生成物 1

HCID 225726422-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxy-6-(2,2,3,3-tetrafluoropropyloxy)pyridine収率 99.2%

試薬・触媒・溶媒 2

HCID 31347Sulfolane溶媒HCID 22335286Ethyl acetate pentane溶媒

反応条件

温度
110 °C

実験手順

To a mixture of 2,2,3,3-tetrafluoropropan-1-ol (0.29 g, 2.2 mmol) in dry sulfolane (2 ml) is added NaH (60% in oil, 0.09 g, 2.2 mmol) and 2,6-bis-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine (0.8 g, 1.8 mmol). After stirring at 110° C. for 3.7 h the mixture is cooled to ambient temperature. The resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed 10 times with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.72 g, 57% yield) of m.p. 73-74° C.

後処理

  1. temperatureis cooled to ambient temperature
  2. filtrationfiltered through a bed of silica gel
  3. washThe filtrate is washed 10 times with water
  4. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

出典と根拠

ORDレコード
ord-facc9139d28f472d8d74f9b9d1df1032
出典データセット
uspto-grants-2005_02
特許番号
US06852673B2

関連ノート

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