Water → HCID 58423229、化合物

HRID 1398026ノート

反応式

HRID 1398026 の反応式
[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].FC(F)(F)S(O[CH2:19][C:20]([F:23])([F:22])[F:21])(=O)=O.O>CN(C=O)C.[Cl-].[Na+].O>[F:1][C:2]1[C:9]([O:10][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 196072232-Fluoro-3-hydroxybenzonitrile

生成物 1

HCID 58423229HCID 58423229、化合物収率 81.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A stirred solution of 2-fluoro-3-hydroxybenzonitrile (800 mg, 5.83 mmol) in DMF (10 mL) at 0° C. was treated portionwise with NaH (280 mg, 7.00 mmol) (60% oil dispersion). The reaction mixture was then stirred for 0.5 h and 2,2,2-trifluoroethyl trifluoromethanesulfonate (1490 mg, 6.42 mmol) was added. The reaction was allowed to warm to rt overnight with stirring. The reaction mixture was then treated with water (40 mL) and brine (5 mL) and extracted with ethyl acetate (˜50 mL). The organic extract was washed with water, dried over anhydrous Na2SO4, filtered and conc. in vacuo to afford a residue which was purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes) to yield the title compound as a white solid (1040 mg, 81%). 1H NMR (400 MHz, MeOD) δ ppm 7.56 (td, 1 H), 7.47-7.38 (m, 1 H), 7.38-7.24 (m, 1 H), 4.73 (q, 2 H); m/z 220.

後処理

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate (˜50 mL)
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered and conc. in vacuo
  7. customto afford a residue which
  8. customwas purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-fee0d2cb4fc144ec9df6cb80da812aba
出典データセット
uspto-grants-2014_12
特許番号
US08901307B2

反応ノート

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