Ammonium Chloride → HCID 23114695、化合物

HRID 2080362ノート

反応式

HRID 2080362 の反応式
C([Mg]Cl)(C)C.[CH2:6]([O:9][C:10]1[C:11](Br)=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:7]=[CH2:8].[F:17][C:18]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:19]=1[CH:20]=[O:21].[Cl-].[NH4+]>O1CCCC1>[CH2:6]([O:9][C:10]1[C:11]([CH:20]([C:19]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:18]=2[F:17])[OH:21])=[N:12][CH:13]=[CH:14][CH:15]=1)[CH:7]=[CH2:8]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 1376632,5-DifluorobenzaldehydeHCID 23028574Pyridine, 2-bromo-3-(2-propenyloxy)-HCID 178418918HCID 178418918、化合物

生成物 1

HCID 23114695HCID 23114695、化合物収率 45.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under an argon atmosphere, a tetrahydrofuran solution (1.5 ml, 3 mmol) of isopropylmagnesium chloride was added dropwise to a tetrahydrofuran (2 ml) solution of the 3-allyloxy-2-bromopyridine (642 mg, 3 mmol) obtained in Referential Example 8 under ice cooling. The resulting mixture was stirred at room temperature for 60 minutes. To the resulting brown solution was added dropwise 2,5-difluorobenzaldehyde (328 μl, 3 mmol) under ice cooling. The temperature of the reaction mixture was gradually raised to room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The solvent was then dried and the residue obtained by concentration under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the title compound (375 mg, 45%) as an oil.

後処理

  1. customobtained in Referential Example 8 under ice cooling
  2. temperatureThe temperature of the reaction mixture was gradually raised to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. customThe solvent was then dried
  5. customthe residue obtained by concentration under reduced pressure
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-9a0ef0f3aae44f69a0a47b02959681d6
出典データセット
uspto-grants-2011_04
特許番号
US07932271B2

反応ノート

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