Thionyl Chloride → HCID 69106520、化合物

HRID 33480ノート

反応式

HRID 33480 の反応式
S(Cl)([Cl:3])=O.[F:5][C:6]([F:22])([F:21])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19]O)=[N:17][CH:18]=2)=[CH:9][CH:8]=1>CN(C)C=O>[Cl:3][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([F:22])([F:21])[F:5])=[CH:8][CH:9]=2)=[CH:18][N:17]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 21936189[5-(4-Trifluoromethyl-phenyl)-pyridin-2-yl]-methanol

生成物 1

HCID 69106520HCID 69106520、化合物収率 23%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

658 mg (0.40 ml, 5.53 mmol) thionyl chloride is added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 700 mg (2.76 mmol) [5-(4-Trifluoromethyl-phenyl)-pyridin-2-yl]-methanol, stirred for 5 min. at 0° C., and at room temperature (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 ethyl acetate. The combined organic phases were washed with water, dried (sodium sulphate), and evaporated. Purification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:4) gave 170 mg (23%) of 2-Chloromethyl-5-(4-trifluoromethyl-phenyl)-pyridine as slightly pink crystals.

後処理

  1. waitat room temperature (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 ethyl acetate
  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 1:4)

出典と根拠

ORDレコード
ord-316b49fa985340f99c4901bf58bce526
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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