Sodium Hydroxide → 2-Methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionic Acid

HRID 1394561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394561
[CH3:1][C:2]([O:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=1)([CH3:7])[C:3]([O:5]C)=[O:4].[OH-].[Na+]>CO.O1CCCC1.O>[CH3:7][C:2]([O:8][C:9]1[CH:14]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:12]=[CH:11][N:10]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 22270531Methyl 2-Methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionate

Produkt 1

HCID 222704912-Methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 2-methyl-2-(4-trifluoromethyl-2-pyridyloxy)propionate (Step B, 7.5 g, 29 mol) in 50 mL of methanol, 50 mL of tetrahydrofuran and 50 mL of water was added sodium hydroxide (2.3 g, 57 mmol). After stirring at 50° C. for 5 h, the reaction mixture was partially concentrated, and was added 2 M hydrochloric acid to pH>2. The resulting mixture was extracted with ethyl acetate (2×200 mL), and the combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 8.28 (d, 1H), 7.17 (d, 1H), 7.05 (s, 1H), 1.70 (s, 6H).

Aufarbeitung

  1. concentrationthe reaction mixture was partially concentrated
  2. additionwas added 2 M hydrochloric acid to pH>2
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×200 mL)
  4. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4065a708a60840bb9b66f58f19774baa
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348456B2

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