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

HRID 709603Notes

Reaction equation

HRID 709603 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[CH:17]=[CH:18][C:19]([C:27](OC)=[O:28])=[N:20][C:21]=1[O:22][CH2:23][CH:24]([CH3:26])[CH3:25].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[CH:17]=[CH:18][C:19]([CH2:27][OH:28])=[N:20][C:21]=1[O:22][CH2:23][CH:24]([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117759827Methyl 5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypicolinate

Product 1

HCID 117760235(5-(2-Fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (250 mg) in diethyl ether (5.0 mL) was added a solution of methyl 5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypicolinate (594 mg) in diethyl ether (2.0 mL) at 0° C., and the mixture was stirred for 1 hr. Water and aqueous sodium hydroxide solution were added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-a44593e85ca4482699d0a523b8a561b2
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…