Lithium Hydroxide → 2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1253658

Reaktionsgleichung

Reaktionsgleichung von HRID 1253658
[Li+].[OH-].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH:10]2NS(C1C(C)=CC(OC)=CC=1C)(=O)=O)=[O:6]>CO.O1CCCC1.O.CC(C)=O>[CH2:12]1[C:13]2[C:9](=[CH:8][C:7]([C:5]([OH:6])=[O:4])=[CH:15][CH:14]=2)[CH2:10][CH2:11]1

Komponenten

7

Edukt 2

HCID 3939Lithium HydroxideHCID 595054523-[[(4-methoxy-2,6-dimethyl-phenyl)sulfonyl]amino]-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester

Produkt 1

HCID 2328412,3-dihydro-1H-indene-5-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

LiOH (5 equiv.) was added to a suspension of 3-[[(4-methoxy-2,6-dimethyl-phenyl)sulfonyl]amino]-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester (C-01) (11.75 mmol) in methanol (40 ml), tetrahydrofuran (40 ml) and water (30 ml) and the reaction mixture was stirred at 25° C. overnight. Methanol and THF were distilled off, the aqueous residue was acidified with 1N HCl and the mixture was filtered. The white solid obtained was taken up in a mixture of 350 ml of acetone and 50 ml of methanol and the mixture was stirred for 1 h. After filtration, the white solid was dried in vacuo to obtain 3-[[(4-methoxy-2,6-dimethyl-phenyl))sulfonyl]amino]-2,3-dihydro-1H-indene-5-carboxylic acid (F-01). Yield: 90%

Aufarbeitung

  1. distillationMethanol and THF were distilled off
  2. filtrationthe mixture was filtered
  3. customThe white solid obtained
  4. stirringthe mixture was stirred for 1 h
  5. filtrationAfter filtration
  6. customthe white solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b37297640fa24fd2a7d29ba28dc6ff54
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455475B2

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