Potassium Cyanide → 3-(2-(4-Fluorophenyl)oxazol-4-yl)-3-hydroxypropanenitrile

HRID 1397421ノート

反応式

HRID 1397421 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13](=[O:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.OP([O-])(O)=O.[K+].[C-:22]#[N:23].[K+]>CN(C=O)C.O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]([OH:15])[CH2:14][C:22]#[N:23])[N:12]=2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 9032Potassium CyanideHCID 516951Monobasic potassium phosphateHCID 673225581-(2-(4-Fluorophenyl)oxazol-4-yl)ethanone

生成物 1

HCID 673225233-(2-(4-Fluorophenyl)oxazol-4-yl)-3-hydroxypropanenitrile収率 21.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

A solution of 1-(2-(4-fluorophenyl)oxazol-4-yl)ethanone (250 mg, 1.22 mmol) in DMF-H2O (7 mL; 2:5 v/v) was cooled to 0° C. and KH2PO4 (327 mg, 2.4 mmol) was added, followed by KCN (116 mg, 1.8 mmol). The reaction mixture was stirred at 80° C. 10 h and then diluted with water. The organic product was extracted with EtOAc and the combined extracts were washed with H2O and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 8-12% EtOAc in petroleum ether) to afford 3-(2-(4-fluorophenyl)oxazol-4-yl)-3-hydroxypropanenitrile (60 mg, yield 21%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.11 (d, J=0.7 Hz, 1H), 8.03-7.98 (dd, J=8.9 Hz, 5.4 Hz, 2H), 7.40-7.34 (t J=8.9 Hz, 2H), 6.13-6.12 (d, J=5.3 Hz, 1H), 4.93-4.87 (m, 1H), 2.98-2.93 (dd, J=8.9 Hz, 5.8 Hz, 2H). MS (ESI) m/z: Calculated for C12H9FN2O2: 232.06. found: 233.0 (M+H)+.

後処理

  1. extractionThe organic product was extracted with EtOAc
  2. washthe combined extracts were washed with H2O and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 8-12% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-d4851385e00f4b9d9b8d09929d6d6ad8
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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