Hydrochloric Acid → 4'-Methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylic acid

HRID 1845265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845265
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([O:23]C)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58188218Methyl 4'-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate

Produkt 1

HCID 581880344'-Methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 4′-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate (60 mg, 0.19 mmol) in tetrahydrofuran (3 mL) was added 2.5 M aqueous lithium hydroxide solution (0.77 mL, 1.9 mmol). The mixture was stirred at room temperature overnight, and then acidified to pH=5 by addition of 2N aqueous HCl and extracted with EtOAc (50 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to afford the title product. 1H NMR (CD3OD, 400 MHz): 8.63 (d, 2H, J=4.8 Hz), 8.16 (t, 1H, J=1.6 Hz), 7.74 (t, 1H, J=2.0 Hz), 7.65 (t, 1H, J=2.0 Hz), 7.56 (d, 2H, J=8.0 Hz), 7.29 (d, 2H, J=8.0 Hz), 7.24 (t, 1H, J=4.8 Hz), 2.39 (s, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c2fcbbe10527462fa13b388eb2201d56
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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