Ethyl 3-(6-methyl-3-pyridyl)propionate → HCID 10057692, compound

HRID 1922293Notes

Reaction equation

HRID 1922293 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3018102Ethyl 3-(6-methyl-3-pyridyl)propionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10057692HCID 10057692, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 3-(6-methyl-3-pyridinyl)propanoate (500 mg, 2.59 mmol) in tetrahydrofuran (15 ml) at 0° C., LiAlH4 (1.42 ml, 2.85 mmol) was added dropwise. When the addition was complete, the ice bath was removed and the reaction stirred at room temperature for 1 hour. Wet THF was added dropwise until a white solid precipitated and the evolution of gas ceased. The solid was filtered off, washed twice with Et2O and the filtrate evaporated under vacuum to afford the title compound (403 mg).

Workup

  1. additionWhen the addition
  2. customthe ice bath was removed
  3. additionWet THF was added dropwise until a white solid
  4. customprecipitated
  5. filtrationThe solid was filtered off
  6. washwashed twice with Et2O
  7. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-8fea223616534dfc9dab2765bd030b0a
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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