4-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehyde → 1-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentan-1-ol

HRID 1669300ノート

反応式

HRID 1669300 の反応式
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[N:7][CH:8]=1.[CH2:19]([Mg]Br)[CH2:20][CH2:21][CH3:22]>C1COCC1>[F:18][C:2]([F:17])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=2)=[N:7][CH:8]=1

参加物

4

反応物 2

HCID 27633594-(5-(Trifluoromethyl)pyridin-2-yl)benzaldehydeHCID 178418682HCID 178418682、化合物

生成物 1

HCID 673422541-[4-(5-Trifluoromethyl-pyridin-2-yl)-phenyl]-pentan-1-ol収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(5-trifluoromethyl-pyridin-2-yl)-benzaldehyde (1.0 g, 3.98 mmol) in andhydrous tetrahydrifuran (THF) (25 mL) that had been cooled to 0° C. in an ice bath is added n-butyl magnesium bromide (8.0 mL, 16.0 mmol) dropwise with stirring under nitrogen. The mixture is allowed to warm slowly to room temperature. The reaction is monitored by HPLC, and upon complete consumption of the aldehyde, quenched with 1N HCl. The mixture is diluted with ethyl ether and water, then extracted. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The title compound is obtained after column chromatography (1.10 g or 3.20 mmol) at 80% yield.

後処理

  1. customupon complete consumption of the aldehyde
  2. customquenched with 1N HCl
  3. additionThe mixture is diluted with ethyl ether and water
  4. extractionextracted
  5. washThe organic layer is washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0d34862f7ae145e693cf5479a557bc1d
出典データセット
uspto-grants-2011_08
特許番号
US07989457B2

反応ノート

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