Methyl 5-fluoro-2-methoxynicotinate → (5-Fluoro-2-methoxypyridin-3-yl)methanol

HRID 509938Notes

Reaction equation

HRID 509938 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[N:6][C:5]=1[O:11][CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:10][C:8]1[CH:9]=[C:4]([CH2:3][OH:2])[C:5]([O:11][CH3:12])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14783852Methyl 5-fluoro-2-methoxynicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 44754796(5-Fluoro-2-methoxypyridin-3-yl)methanolYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-fluoro-2-methoxy-nicotinic acid methyl ester (35, 10 g, 54.0 mmol) in 200 mL of tetrahydrofuran, lithium aluminum hydride (81 mL, 1 M in tetrahydrofuran, 81 mmol) was added dropwise at −78° C. and stirred for several hours. The reaction was quenched with dropwise addition of 3 mL water, 3 mL of 15% aqueous sodium hydroxide, and 10 mL of water sequentially, then 200 mL of methyl t-butyl ether was added. Solids were filtered out and the filtrate concentrated under vacuum to provide the desired compound as a white solid (36, 8 g, 50.9 mmol, 94%).

Workup

  1. customThe reaction was quenched with dropwise addition of 3 mL water, 3 mL of 15% aqueous sodium hydroxide, and 10 mL of water sequentially
  2. addition200 mL of methyl t-butyl ether was added
  3. filtrationSolids were filtered out
  4. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-b29179959d2949238ba087f904f9435b
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

Loading…