Hydrochloric Acid → 5-(2-Pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acid

HRID 713742

Reaktionsgleichung

Reaktionsgleichung von HRID 713742
C[O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:10][C:8]=2[CH:9]=1)=[O:4].[OH-].[Li+].Cl>O1CCOCC1>[N:17]1([CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:7]3[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][C:8]=3[CH:10]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 666882085-(2-Pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acid methyl ester

Produkt 1

HCID 229283195-(2-Pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acidAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of 5-(2-pyrrolidin-1-ylethoxy)benzofuran-2-carboxylic acid methyl ester (960 mg, 3.3 mmol) anhydrous ethylene glycol dimethyl ether (10 ml) was added dropwise degassed aqueous lithium hydroxide solution (2.0 ml, 2.0M). After stirring at room temperature for 4 h, the solution was cooled down and the pH was adjusted to 2 with 4.0 M HCl in dioxane. A gummy tan precipitate formed. The solvent was removed and the gummy residue was frozen and lyophilized. The tan colored solid was dissolved in boiling 2-propanol (90 ml), the solution was filtered hot and then cooled to give 5-(2-pyrrolidin-1-yl-ethoxy)-benzofuran-2-carboxylic acid as beige colored needles (528 mg). Additional 153 mg was obtained from the mother liquor.

Aufarbeitung

  1. temperaturethe solution was cooled down
  2. customA gummy tan precipitate formed
  3. customThe solvent was removed
  4. temperaturethe gummy residue was frozen
  5. dissolutionThe tan colored solid was dissolved
  6. filtrationthe solution was filtered hot
  7. temperaturecooled

Quellen und Nachweise

ORD-Eintrag
ord-378c2720e59548e6bb932de01f7db69b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09186347B1

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