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

HRID 709771Notes

Reaction equation

HRID 709771 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])=[C:18]([O:31][CH3:32])[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]=[C:18]([O:31][CH3:32])[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 117760172Methyl 6-(2-fluoro-5-methoxyphenyl)-5-isobutoxy-2-methoxynicotinate

Product 1

HCID 117760272(6-(2-Fluoro-5-methoxyphenyl)-5-isobutoxy-2-methoxypyridin-3-yl)methanolYield 661.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (67 mg) in diethyl ether (2.0 mL) was added a solution of methyl 6-(2-fluoro-5-methoxyphenyl)-5-isobutoxy-2-methoxynicotinate (213 mg) in diethyl ether (1.0 mL) at 0° C., and the mixture was stirred for 20 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 evaporated to give a crude product of the title compound (1.30 g) as an orange oil. This compound was used for the next step without further purification.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. customThe solvent in the filtrate was evaporated

Sources & evidence

ORD record
ord-46eadaf4e20549439a8ba6bb31e65582
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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