Sodium Hydroxide → 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 854938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854938
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12][CH3:13])[CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2.[OH-].[Na+]>C1COCC1.CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12][CH3:13])[CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 69517271ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Produkt 1

HCID 589345476-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18504229Ethanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate (Step 3, 0.203 g, 0.575 mmol) in THF:EtOH:H2O (7:2:1, 5 mL), was added aqueous sodium hydroxide (0.63 mmol, 0.25 mL of 2.5 N soln.) and allowed to stir for two days. The resulting clear, yellow solution was concentrated in vacuo, was diluted with water (35 mL), and was acidified with concentrated HCl resulting in formation of a yellow suspension. Vacuum filtration of the suspension yielded the title compound as a yellow powder (0.132 g, 71%). 1HNMR (acetone-d6/300 MHz) 7.87 (s, 1H), 7.34 (d, J=2.2 Hz, 1H), 7.25 (d, J=2.2 Hz, 1H), 5.93 (q, 1H, J=7.05 Hz), 2.53 (s, 3H). LRMS m/z 323 (M−H); ESHRMS m/z 322.9782 (M−H, C12H7F3O3ClS, Calc'd 322.9757). Anal. Calc'd for C12H8F3O3ClS: C, 44.39; H, 2.48. Found: C, 44.63; H, 2.52.)

Aufarbeitung

  1. concentrationThe resulting clear, yellow solution was concentrated in vacuo
  2. additionwas diluted with water (35 mL)
  3. filtrationVacuum filtration of the suspension

Quellen und Nachweise

ORD-Eintrag
ord-e28846c605c94fb6b05624c8b10243aa
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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