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

HRID 1911168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911168
[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 52b (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 52c (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-bf932ab43fde4feea09d99f8abb35325
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604017B2

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