Lithium hydroxide, monohydrate → 5-Phenylbenzo[b]thiophene-2-carboxylic acid

HRID 409897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409897
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]3[S:11][C:12]([C:14]([O:16]C)=[O:15])=[CH:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[Li].O>C1COCC1.O>[C:1]1([C:7]2[CH:19]=[CH:18][C:10]3[S:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 19007392Methyl 5-phenylbenzo[b]thiophene-2-carboxylate

Produkt 1

HCID 596260715-Phenylbenzo[b]thiophene-2-carboxylic acidAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of compound 10c (510 mg, 1.9 mmol) and LiOH.H2O (319 mg, 7.6 mmol) in THF/H2O (10/10 mL) was stirred at room temperature overnight. The resulting mixture was concentrated and diluted with water. The water layer was acidified with 1N aqueous HCl to pH˜4 and extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated to give 10d (479 mg), which was used in the next reaction without further purification. MS m/z (M+H+) 255.0.

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8da277fb9036411caf8c0d4615339046
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759533B2

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