Lithium hydroxide, monohydrate → 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 855024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855024
[I:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7]2.O.[OH-].[Li+]>O1CCCC1.O>[I:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58934894ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Produkt 1

HCID 589344428-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acidAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the solution of 0.4 g (0.93 mmol) of ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 8 mL of tetrahydrofuran was added a solution of 155 mg (3.7 mmol) of lithium hydroxide hydrate (LiOH—H2O) in 15 mL of water. The resulting solution was heated to reflux for one h. After cooling to room temperature, the volatiles were removed, the residue was acidified at 0° C. to pH=1.5 with dilute hydrochloric acid. The product was extracted with ethyl ether. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and concd in vacuo to afford 0.30 g (81%) of a light yellow solid: 1H NMR (CDCl3/400 MHz) 7.67(s, 1H), 7.18(d, J=8.4 Hz, 1H), 6.51(d, J=8.4 Hz, 1H), 5.78(q, J=6.8 Hz, 1H), 3.92(s, 3H). MS (ESI+) 400.9 (M+1, 100). MS(ES−) 398.9(M−H, 100). HRMS (ES−) m/z calcd for (M−H; C12H7F3O4): 398.9336, found 398.9368.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for one h
  3. customthe volatiles were removed
  4. customwas acidified at 0° C. to pH=1.5 with dilute hydrochloric acid
  5. extractionThe product was extracted with ethyl ether
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate and concd in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b5a7d543e97842baa59caa545ab1d23b
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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