Lithium hydroxide, monohydrate → 3-[4-(4-Isopropyl-phenyl)-pyridin-2-yl]-benzoic acid

HRID 628836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628836
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O.[OH-].[Li+]>CO.O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 69232425Ethyl 3-[4-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate

Produkt 1

HCID 116166883-[4-(4-Isopropyl-phenyl)-pyridin-2-yl]-benzoic acidAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

Part E. A solution of ethyl 3-[4-(4-isopropyl-phenyl)-pyridin-2-yl]-benzoate (116 mg, 0.34 mmol) in methanol-water (3 mL/1 mL) is treated with lithium hydroxide hydrate (41 mg, 1.7 mmol). The mixture is stirred at ambiemperature for 12 h., then partitioned between water and diethyl ether. The aqueous phase is neutralized to pH 7 with 3 N aq. HCl and extracted with ethyl acetate. The extract is washed with brine, dried over magnesium sulfate, filtered and evaporated to afford the title compound as a white powder (92 mg, 85%), m.p. 233-234° C. 1H NMR (300 MHz, methanol-d4): δ 8.66 (1H, s), 8.65 (1H, d, J=8 Hz), 8.25 (1H, d, J=8 Hz), 8.14-8.11 (2H, m), 7.78 (2H, d, J=9 Hz), 7.69-7.62 (2H, m), 7.42 (2H, d, J=9 hz), 3.00 (1H, heptet, J=7 Hz), 1.30 (6H, d, J=7 Hz). MS (ES+): m/e x. MS (ES−): m/e 319 (20), 318 (100).

Aufarbeitung

  1. custompartitioned between water and diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-eacd134d1bf742cd9958d01881426817
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315467B2

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