Aluminium lithium hydride → HCID 86625534, compound

HRID 2266021Notes

Reaction equation

HRID 2266021 reaction equation
[CH2:1]([C:3]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:4]=1[C:5](N(OC)C)=[O:6])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([C:3]1[C:4]([CH:5]=[O:6])=[CH:11][CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[N:14]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59598165HCID 59598165, compound

Product 1

HCID 86625534HCID 86625534, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a cooled (−78° C.) solution of 2-ethyl-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (113 mg, 0.43 mmol) in THF (4 mL) was added lithium aluminum hydride (1M LAH in THF, 0.22 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-ethyl-6-trifluoromethyl-pyridine-3-carbaldehyde quantitatively as oil. The crude product was used directly in the following reaction.

Workup

  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

Sources & evidence

ORD record
ord-c09692f65bac4c1ebd966a2df79f3777
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

Loading…