Methyl 6-methoxypyridine-3-carboxylate → (2-Methoxypyridin-4-yl)methanol

HRID 1955812Notes

Reaction equation

HRID 1955812 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6](C(OC)=O)=[CH:5][N:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:22][CH2:21]C1>C1COCC1>[OH:22][CH2:21][C:11]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

4

Reactant 2

HCID 586039Methyl 6-methoxypyridine-3-carboxylateHCID 68718528lithium aluminium hydride THF

Product 1

HCID 14462410(2-Methoxypyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a 0° C. THF (70 mL) solution of methyl 6-methoxynicotinate (6.0 g, 36 mmol) was added 36 mL of 1M LAH/THF. The reaction, after stirring at 20° C. for two hours, was quenched with aq. NH4Cl, diluted with aq. HCl until all salts dissolved, and extracted with EtOAc (3×) after adjusting the pH to 5. The crude 4-hydroxymethyl-2-methoxypyridine (1.75 g), obtained after drying and concentration of the EtOAc layers, was converted to 4-methoxy-3-pyridinylcarboxaldehyde following the procedure described in step A of Example 123. The title compound was prepared from 4-methoxy-3-pyridinylcarboxaldehyde following the procedure described in step A of Example 119.

Workup

  1. customTo a 0° C
  2. customThe reaction
  3. customwas quenched with aq. NH4Cl
  4. additiondiluted with aq. HCl until all salts
  5. dissolutiondissolved
  6. extractionextracted with EtOAc (3×)

Sources & evidence

ORD record
ord-b7e591c1d09f4c468be1e9643ab462df
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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