Benzyl Alcohol → 3-Benzyloxy-5-(Trifluoromethyl)Pyridine

HRID 617335

反応式

HRID 617335 の反応式
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:21][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 27366983-Chloro-5-(trifluoromethyl)pyridine

生成物 1

HCID 218518253-Benzyloxy-5-(Trifluoromethyl)Pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a 3.63 g (20 mmol) sample of 3-chloro-5-trifluoromethylpyridine dissolved in 15 mL of DMF and cooled to 0° C. was added 960 mg of NaH (60%), 2.07 mL of benzyl alcohol was added slowly. The reaction mixture was stirred for 2 hours at 40° C. The solvent was then evaporated in vacuo and the mixture diluted with chloroform, washed with saturated NaHCO3 and a brine solution. The organic layer was then dried over MgSO4. The resulting crude material was purified by flash chromatography on silica gel to give the title product. MS (DCI/NH3) m/e 154 (M+H)+. 1H NMR (CDCl3, 300 MHz) d: 8.56 (d, J=1.8 Hz, 1H), 8.47 (d, J=0.9 Hz, 1H), 7.51 (dd, J=1, 0.9 Hz, 1H).

後処理

  1. additionwas added slowly
  2. customThe solvent was then evaporated in vacuo
  3. additionthe mixture diluted with chloroform
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organic layer was then dried over MgSO4
  6. customThe resulting crude material was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-5af9cf79592a411eacdd36a2ff679154
出典データセット
uspto-grants-1999_09
特許番号
US05948793

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