Hydrochloric Acid → 5-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid

HRID 1799118

Reaktionsgleichung

Reaktionsgleichung von HRID 1799118
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([O:21]CC)=[O:20].[Li+].[OH-].Cl>CO.C1COCC1.O.[Cl-].[Na+].O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([OH:21])=[O:20]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67434696Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate

Produkt 1

HCID 585519085-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate (2.6 g, 7.9 mmol) was dissolved in MeOH/THF (1:1, 60 mL) and a solution of LiOH (378 mg, 15.7 mmol) in H2O (15 mL) was added. The reaction was stirred for ˜5 h and the pH adjusted to ˜3 by the addition of 3N HCl. The mixture was poured into brine and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4) and concentrated. The crude product was crystallized from EtOAc to give 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid (1.8 g, 75% yield).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was crystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-1e746c0d83bc4567ac42d22fe8ca3095
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343997B2

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