Aluminium lithium hydride → 3-(6-Methoxypyridin-3-yl)propan-1-ol

HRID 53205Notes

Reaction equation

HRID 53205 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](OC)=[O:18])=[CH:11][N:10]=1>C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22009636Methyl 3-(2-methoxy-5-pyridyl)propionate

Product 1

HCID 215852063-(6-Methoxypyridin-3-yl)propan-1-olYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.56 g (1.1 eq) of LAH in 50 ml of dry THF at 5° C. under nitrogen was added a solution of 2.7 g (13.5 mmol) of methyl 3-(2-methoxy-pyridin-5-yl)-propionate in THF and the reaction mixture was stirred at room temperature for 2 h. The mixture was quenched with 0.6 ml of water, 0.6 ml of 10% NaOH, and 1.8 ml of water successively. The mixture was filtered and the filtrate was concentrated in vacuo to yield 2.0 g (87%) of 2-methoxy-5-(3-hydroxypropyl)-pyridine as a yellow oil.

Workup

  1. customThe mixture was quenched with 0.6 ml of water, 0.6 ml of 10% NaOH, and 1.8 ml of water successively
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3cae4738078f4cd1abfe90ac16d31f67
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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