Lithium Hydroxide → HCID 23441961, compound

HRID 1419835Notes

Reaction equation

HRID 1419835 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([C:25]([O:27]CC)=[O:26])[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[CH:19]=2)[C:10]([F:30])=[C:9]([CH3:31])[C:8]=1[F:32])#[N:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:16]([C:25]([OH:27])=[O:26])[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[CH:19]=2)[C:10]([F:30])=[C:9]([CH3:31])[C:8]=1[F:32])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86584668HCID 86584668, compound

Product 1

HCID 23441961HCID 23441961, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To 5-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]benzene-1,3-dicarboxylic acid, diethyl ester (0.97 g, 2.0 mmol) in tetrahydrofuran/water (20 mL, 1/1) was added lithium hydroxide (0.42 g, 10 mmol). After heating at 60° C. for 90 minutes, the material was partitioned between ethyl acetate and 2N HCl. The organic layer was separated, dried (MgSO4), and the solvent removed in vacuo to give 5-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]benzene-1,3-dicarboxylic acid; NMR (DMSO) 8.25 (s,1), 7.85 (s,2), 7.4-7.7 (m,3), 7.3 (m,3), 2.4 (s,3) ppm.

Workup

  1. customthe material was partitioned between ethyl acetate and 2N HCl
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9fe42d62c02e48bf90de80b1ef6c5678
Source dataset
uspto-grants-1999_03
Patent number
US05889005

Reaction notes

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