Aluminium lithium hydride → HCID 59635809, compound

HRID 406748Notes

Reaction equation

HRID 406748 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH:10]([CH3:20])[CH2:11][N:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]1=[O:19]>O1CCCC1>[Br:18][C:15]1[CH:16]=[CH:17][N:12]([CH2:11][CH:10]([CH3:20])[CH2:9][OH:8])[C:13](=[O:19])[CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 59635795Methyl 4-bromo-α-methyl-2-oxo-1(2H)-pyridinepropanoate

Product 1

HCID 59635809HCID 59635809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1 M solution in tetrahydrofuran, 1.16 mL) was added to a solution of 3-(4-bromo-2-oxo-2H-pyridin-1-yl)-2-methyl-propionic acid methyl ester (0.53 g) in tetrahydrofuran (6 mL) chilled in an ice bath. After stirring the solution with cooling for 2 h, another portion of LiAlH4 (1 M in tetrahydrofuran, 0.29 mL) was added. After stirring with cooling for 1 more hour, the reaction was quenched by the addition of water. The resulting mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was evaporated to give the title compound. Yield: 0.37 g (78% of theory); Mass spectrum (ESI+): m/z=246/248 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. temperaturewith cooling for 2 h
  3. stirringAfter stirring
  4. temperaturewith cooling for 1 more hour
  5. customthe reaction was quenched by the addition of water
  6. extractionThe resulting mixture was extracted with ethyl acetate
  7. washthe combined organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fadeb6e8963f45b087501d85cbb7b20f
Source dataset
uspto-grants-2014_06
Patent number
US08754076B2

Reaction notes

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