Aluminium lithium hydride → HCID 67508360, compound

HRID 715348Notes

Reaction equation

HRID 715348 reaction equation
[CH3:1][C:2]1[C:3]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][C:2]1[CH:11]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:12][CH2:13][C:14]([F:17])([F:15])[F:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67508999HCID 67508999, compound

Product 1

HCID 67508360HCID 67508360, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5-methyl-6-(2,2,2-trifluoroethoxy)nicotinate (0.80 g, 3.21 mmol, Step-1) in THF (10 mL) is added slowly lithium aluminum hydride (0.11 g, 3.21 mmol) at 0° C. The resulting mixture is stirred at rt for 1 hour. The reaction mixture is carefully quenched with 25% aqueous ammonia solution at 0° C. Then the mixture is diluted with DCM (50 mL) and celite is added to the mixture. After stirring at rt for 1 hour, the mixture is filtrated through a pad of Celite, and the filtrate is concentrated in vacuo to give 0.70 g (99% yield) of the title compound as colorless oil. This material is used for the next reaction (Step-3) without further purification.

Workup

  1. customThe reaction mixture is carefully quenched with 25% aqueous ammonia solution at 0° C
  2. additionThen the mixture is diluted with DCM (50 mL) and celite
  3. additionis added to the mixture
  4. stirringAfter stirring at rt for 1 hour
  5. filtrationthe mixture is filtrated through a pad of Celite
  6. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-40fc99037ffd466bb79ef7d86fcbef3a
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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