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

HRID 2265988

반응식

HRID 2265988 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 288753222-Methyl-6-(trifluoromethyl)nicotinaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-adf0009457f64c29bc936bb352070a78
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858621B2

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