Lithium Hydroxide → 2-(1-(Methylsulphonyl)indolin-5-yl)propanoic acid

HRID 2194930

Reaktionsgleichung

Reaktionsgleichung von HRID 2194930
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[Li+].[OH-]>C1COCC1.O>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 58093552Ethyl 2-(1-(methylsulphonyl)indolin-5-yl)propanoate

Produkt 1

HCID 580935782-(1-(Methylsulphonyl)indolin-5-yl)propanoic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

the propanoate (1.78 mmol, 0.53 g) obtained in step b was dissolved in a THF-water mixture (5 ml, 2:1), LiOH (5.34 mmol, 0.128 g) was added and refluxing was carried out for 12 h. The reaction mixture was extracted with diethyl ether (25 ml), the aqueous phase was acidified to pH 2 with 1 N HCl and extraction was carried out with EE (3×25 ml). The combined organic phases were dried over magnesium sulphate and the solvent was removed in a vacuum. It was possible to obtain 2-(1-(methylsulphonyl)indolin-5-yl)propanoic acid in an 80% yield (0.382 g).

Aufarbeitung

  1. additionwas added
  2. temperaturerefluxing
  3. extractionThe reaction mixture was extracted with diethyl ether (25 ml)
  4. extractionthe aqueous phase was acidified to pH 2 with 1 N HCl and extraction
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customthe solvent was removed in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-93cd678443bc4f3992230c0e152e0e77
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334315B2

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