Water → (6-(2-Fluoro-5-methoxyphenyl)-5-isobutoxypyridin-3-yl)methanol

HRID 709763Notes

Reaction equation

HRID 709763 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[C:25]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][N:17]=1.O.[OH-].[Na+]>C(OCC)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[N:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:24][C:25]=1[O:26][CH2:27][CH:28]([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117760303Methyl 6-(2-fluoro-5-methoxyphenyl)-5-isobutoxynicotinate

Product 1

HCID 117760274(6-(2-Fluoro-5-methoxyphenyl)-5-isobutoxypyridin-3-yl)methanolYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (622 mg) in diethyl ether (20 mL) was added a solution of methyl 6-(2-fluoro-5-methoxyphenyl)-5-isobutoxynicotinate (1.82 g) in diethyl ether (5.0 mL) at 0° C., and the mixture was stirred for 30 min. Water and aqueous sodium hydroxide solution were added to the reaction mixture, and the resulting precipitate was filtered off. The solvent in the filtrate was concentrated, and the residue was recrystallized (ethyl acetate/hexane) to give the title compound (1.30 g) as a white solid.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. concentrationThe solvent in the filtrate was concentrated
  3. customthe residue was recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c99ea0d6b023442a89191a7843233296
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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