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

HRID 2265988Notes

Reaction equation

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

Participants

Conditions

Temperature: -10 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-adf0009457f64c29bc936bb352070a78
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858621B2

Reaction notes

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