Lithium hydroxide, monohydrate → [6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid

HRID 1644722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1644722
C([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:15]=[C:14]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:28])[CH:12]=2)[CH:7]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[F:28][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH2:5][C:4]([OH:29])=[O:3])[CH:15]=[C:14]2[C:16](=[O:27])[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59350811[6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

Produkt 1

HCID 46204884[6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acidAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (0.63 g, 1.52 mmol) in tetrahydrofuran (6 mL) and water (6 mL) was added lithium hydroxide monohydrate (0.83 g, 1.98 mmol). The reaction mixture was heated at reflux for 3 hours. After cooling to room temperature, more water was added, and tetrahydrofuran was removed under reduced pressure. The pH was adjusted to 2 with ca. 2 mL of 4 N hydrochloric acid. The resulting light tan solid was collected by filtration to give pure [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid (0.53 g, 90%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customtetrahydrofuran was removed under reduced pressure
  4. filtrationThe resulting light tan solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-fc8bc5a25e154c7391f3950590752e1e
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124629B2

Notizen zur Reaktion

Wird geladen…