Lithium Hydroxide → HCID 15614005, compound

HRID 2244028Notes

Reaction equation

HRID 2244028 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[C:15]([OH:22])[C:14]=2[CH2:23][CH2:24][CH3:25])[N:6]=1)=[O:4].[OH-].[Li+]>CO.O>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][CH:8]=2)=[C:14]([CH2:23][CH2:24][CH3:25])[C:15]=1[OH:22])(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19752431HCID 19752431, compound

Product 1

HCID 15614005HCID 15614005, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve 6-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-pyridine-2-carboxylic acid methyl ester (3.77 g, 10.9 mmol) in MeOH (20 mL) and water (5 mL). Add 2N aqueous lithium hydroxide (10.9 mmol). After 12 hours, concentrate under reduced pressure and dissolve the residue in 4N hydrochloric acid in dioxane. Add water until white precipitate forms and collect by filtration to yield the title compound as a white solid (2.30 g, 6.99 mmol): 1H NMR (d6-DMSO) δ 0.89 (t, 3H), 1.50 (m, 2H), 2.56 (s, 3 H), 2.63 (t, 3H), 5.31 (s, 2H), 6.57 (d, 1H), 7.47 (m, 1H), 7.67 (d, 1H), 7.93 (m, 2H), 12.84 (s, 1H), (acid proton not observed); mass spectrum (m/e): 328 (M−1).

Workup

  1. concentrationconcentrate under reduced pressure
  2. dissolutiondissolve the residue in 4N hydrochloric acid in dioxane
  3. filtrationAdd water until white precipitate forms and collect by filtration

Sources & evidence

ORD record
ord-a24bcf50e7ca454084e5e5848f538de3
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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