Sodium Hydroxide → HCID 7130760, Verbindung

HRID 1892085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1892085
[OH-].[Na+].[C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]([O:16]C)=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>O.C1COCC1.CO>[C:3]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 12317965Methyl 5-(4-phenylphenyl)thiophene-2-carboxylate

Produkt 1

HCID 7130760HCID 7130760, VerbindungAusbeute 80,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of sodium hydroxide in water (2N, 50 mL) was added to a suspension of compound 1022 (3.5 g, 11.9 mmol) in THF (50 mL) and methanol (50 mL). The reaction mixture was stirred at room temperature for 14 hours and then concentrated to approximately 1/10 of its original volume (15 mL). The concentrated solution was adjusted to pH 2-3 using 2N aqueous hydrochloric acid solution and extracted with a mixture of DCM and ethanol (7:3 ratio, 200 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give the compound 1023 (2.7 g). 1H NMR (CDCl3, 300 MHz) δ 7.39-7.41 (d, 1H), 7.46-7.51 (m, 2H), 7.63-7.64 (d, 1H), 7.71-7.85 (m, 7H).

Aufarbeitung

  1. concentrationconcentrated to approximately 1/10 of its original volume (15 mL)
  2. extractionextracted with a mixture of DCM and ethanol (7:3 ratio, 200 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-52516047c3af431aa501bf349d058796
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507647B2

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