Aluminium lithium hydride → 2-Methyl-6-(trifluoromethyl)nicotinaldehyde

HRID 2265988ノート

反応式

HRID 2265988 の反応式
CON(C)[C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:16][C:7]1[C:6]([CH:4]=[O:5])=[CH:11][CH:10]=[C:9]([C:12]([F:14])([F:13])[F:15])[N:8]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 86625530N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide

生成物 1

HCID 288753222-Methyl-6-(trifluoromethyl)nicotinaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

To a cooled (−78° C.) solution of N-methoxy-N-methyl-2-methyl-6-trifluoromethyl-3-pyridinecarboxamide (615 mg, 2.48 mmol) in THF (10 mL) was added lithium aluminum hydride (LAH, 1 N/THF, 1.23 mL). The mixture was stirred for 15 minutes, and then warmed to −10° C. After additional stirring for 30 minutes, the mixture was quenched with saturated potassium hydrogen sulfate solution (1 mL) and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give 2-methyl-6-trifluoromethyl-3-pyridinecarboxaldehyde quantitatively as oil. The crude product was used directly in the following reaction.

後処理

  1. stirringAfter additional stirring for 30 minutes
  2. customthe mixture was quenched with saturated potassium hydrogen sulfate solution (1 mL)
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-adf0009457f64c29bc936bb352070a78
出典データセット
uspto-grants-2010_12
特許番号
US07858621B2

反応ノート

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