Water → 7-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17355

反応式

HRID 17355 の反応式
[F:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]2[C:10]=1[O:9][C:8]([C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])=[N:7]2.F[B-](F)(F)F.[H+].[CH3:31][Si](C=[N+]=[N-])(C)C.O>C(Cl)Cl>[F:1][C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]2[C:10]=1[O:9][C:8]([C:11]([CH3:15])([CH3:14])[CH2:12][O:13][CH3:31])=[N:7]2

参加物

6

反応物 4

HCID 962WaterHCID 28118Tetrafluoroboric acidHCID 167693Trimethylsilyldiazomethane2 回HCID 685859577-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685855317-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

7-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-99) (50 mg, 0.15 mmol) was dissolved in methylene chloride (0.5 ml), aqueous 42% tetrafluoroboric acid solution (32 μl, 0.15 mmol) was added, then with cooling with ice, trimethylsilyldiazomethane (2 M hexane solution, 77 μl, 0.15 mmol) was dropwise added, followed by stirring at 0° C. for 10 minutes, further trimethylsilyldiazomethane (2 M, hexane solution, 77 μl, 0.15 mmol) was dropwise added, followed by stirring at 0° C. for 1 hour. After the reaction, water was added followed by extraction with methylene and washing with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative thin-layer silica gel column chromatography, eluted with n-hexane/ethyl acetate (5:1, v/v) to obtain the entitled compound (41.2 mg, 79%) as a colorless transparent oily substance.

後処理

  1. additionwas dropwise added
  2. stirringby stirring at 0° C. for 1 hour
  3. additionwas added
  4. extractionfollowed by extraction with methylene
  5. washwashing with saturated brine
  6. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. washeluted with n-hexane/ethyl acetate (5:1

出典と根拠

ORDレコード
ord-7ca364c2b9624ab2a5b8c527332b1845
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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