Sodium Hydroxide → HCID 21883628, Verbindung

HRID 2214862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214862
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[O:22])[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.[OH-].[Na+]>C1COCC1.CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[O:22])[C:5]2[O:10][CH:9]([C:11]([F:13])([F:14])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 21883599HCID 21883599, Verbindung

Produkt 1

HCID 21883628HCID 21883628, VerbindungAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18504229Ethanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a stirred solution of the ester (Step 3)(0.284 g, 0.849 mmol) in THF:EtOH:H2O (7:2:1, 5 mL) was added aqueous NaOH solution (0.41 mL of 2.5 M, 1.02 mmol). After stirring 40 hours, the reaction was partially concentrated in vacuo to remove the organic solvents, diluted with H2O, washed with diethyl ether, sparged with nitrogen to remove trace diethyl ether, and acidified with concentrated HCl yielding a suspension. Vacuum filtration of the suspension yielded the title compound as a pale yellow powder (0.160 g, 23%). mp 243.3–252.4° C. 1H NMR (acetone-d6/300 MHz) 10.39 (s, 1H), 7.98 (s, 1H), 7.88 (d, 1H, J=2.6 Hz), 7.75 (d, 1H, J=2.6 Hz), 6.08 (q, 1H, J=6.9 Hz). FABLRMS m/z 307 (M+H). ESHRMS m/z 304.9839 (M−H, Calc'd 304.9828). Anal. Calc'd for C12H6Cl1F3O4: C, 47.01; H, 1.97. Found: C, 46.64; H, 1.86.

Aufarbeitung

  1. concentrationthe reaction was partially concentrated in vacuo
  2. customto remove the organic solvents
  3. additiondiluted with H2O
  4. washwashed with diethyl ether
  5. customsparged with nitrogen
  6. customto remove trace diethyl ether
  7. filtrationVacuum filtration of the suspension

Quellen und Nachweise

ORD-Eintrag
ord-d24669c6c82a41979ffe8a04d0c53b27
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109211B2

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