Dimethylformamide → 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine

HRID 33512ノート

反応式

HRID 33512 の反応式
S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:13]=[C:14]([C:18]2[N:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1>ClCCl>[Cl:3][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:27])([F:26])[F:10])[CH:13]=2)=[N:23][CH:22]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24729887(6-(3-(Trifluoromethyl)phenyl)pyridin-3-YL)methanol

生成物 1

HCID 691065005-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine収率 72.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

911 mg (0.56 ml, 7.66 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 970 mg (3.83 mmol) [6-(3-Trifluoromethyl-phenyl)-pyridine-3-yl]-methanol in 30 ml dichloromethane, stirred for 5 min. at 0° C., and at r.t. for 1 h. The mixture is poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), and evaporated. Purification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 750 mg (72%) of 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine as light yellow crystals

後処理

  1. waitat r.t. for 1 h
  2. additionThe mixture is poured on ice/sodium bicarbonate solution
  3. customthe organic phase separated
  4. extractionThe water phase is extracted with dichloromethane
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (sodium sulphate)
  7. customevaporated
  8. customPurification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3)

出典と根拠

ORDレコード
ord-d6c9e3c17fa240de9127e0949efdfbda
出典データセット
uspto-grants-2008_09
特許番号
US07429605B2

反応ノート

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