Sulfuric Acid → 5-(Hydroxy-pyridin-2-yl-methyl)-4'-methyl-biphenyl-3-carboxylic acid

HRID 1845271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845271
[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:3]1[CH:4]=[C:5]([C:16]([O:18]CC)=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1.[OH-].[Li+].OS(O)(=O)=O>O1CCOCC1.O>[OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:3]1[CH:4]=[C:5]([C:16]([OH:18])=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 58188330Ethyl 5-(hydroxy(pyridin-2-yl)methyl)-4'-methylbiphenyl-3-carboxylate

Produkt 1

HCID 581883005-(Hydroxy-pyridin-2-yl-methyl)-4'-methyl-biphenyl-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Ethyl 5-(hydroxy(pyridin-2-yl)methyl)-4′-methylbiphenyl-3-carboxylate (319 mg, 0.92 mmol) was dissolved in 1,4-dioxane (6 mL) and water (0.3 mL). To the stirred solution was added lithium hydroxide (120 mg, 5.0 mmol) and the reaction mixture was stirred at room temperature until the reaction was complete. The mixture was cooled and acidified with 2N aq. H2SO4 to pH 5-6 and extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to yield a light yellow solid. 1H NMR (400 MHz, CD3OD): 8.47 (m, 1H), 8.13 (t, 1H, J=1.6 Hz), 8.02 (t, 1H, J=1.6 Hz), 7.91 (t, 1H, J=1.6 Hz), 7.87 (td, 1H, J=7.6, 1.6 Hz), 7.71 (d, 1H, J=8.0 Hz), 7.51 (d, 2H, J=8.0 Hz), 7.31 (ddd, 1H, J=7.6, 5.2, 1.2 Hz), 7.27 (d, 2H, J=8.0 Hz), 5.93 (s, 1H), 2.37 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (20 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto yield a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-0598d9317c4d4db8b421a98b08097892
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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