Hydrochloric Acid → 6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic Acid

HRID 854859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854859
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Cl)[C:11]=1O)[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-].[Li+].Cl>CO.C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:15])[F:16])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69517486ethyl 6,8-dichloro-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Produkt 1

HCID 97956526-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic AcidAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21864137Acetonitrile methanol waterLösungsmittel

Versuchsvorschrift

A solution of the ester from Step 2 (0.20 g, 0.56 mmole) was dissolved in 3 mL mixture of MeOH/ACN/H2O=1/1/1, treated with lithium hydroxide (81 mg, 3.36 mmole) and stirred at room temperature for 2 days. The reaction mixture was acidified with 1.0 N HCl to pH=1 and was extracted with EtOAc. The organic layer was washed with water,dried over anhydrous MgSO4, and filtered. The filtrate was evaporated and dried in vacuo to afford the title compound as a yellow solid (0.11 g, 60%): ESHRMS m/z 326.9438 (M−H, C11H4O4F3Cl2, Calc'd 326.9433). 1H NMR (acetone-d6/400 MHz) 7.82 (s, 1H), 7.46(s, 1H), 6.00 (q, 1H, J=7.0 Hz).

Aufarbeitung

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with water,dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3770f3cbda164067a85a93dcf4b83e9e
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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