Lithium Hydroxide → 3-(1,3-Thiazol-2-yl)benzoic acid

HRID 1455373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455373
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=[O:10].[OH-].[Li+]>C1COCC1.O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([OH:11])=[O:10]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 18945333Methyl 3-thiazol-2-yl-benzoate

Produkt 1

HCID 210750873-(1,3-Thiazol-2-yl)benzoic acidAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Preparation H11, Step 4: A solution of 0.6 g (0.0027 mol) of methyl 3-(thiazol-2-yl)benzoate in 6 ml of THF and 1.2 ml of water was charged with 0.11 g (0.0046 mol) of lithium hydroxide. The reaction mixture was stirred at RT overnight. THF was removed and the aqueous layer was washed with ether and acidified with 1.5 N HCl. The solid product was extracted with ethyl acetate. The organic layer was washed with brine and concentrated to afford 3-(thiazol-2-yl)benzoic acid (0.4 g) as an off white solid obtained. 1H NMR (400 MHz, CDCl3): 7.45 (d, 1H), 7.63 (m, 1H), 8.0 (d, 1H), 8.22 (d, 1H), 8.30 (d, 1H), 8.79 (s, 1H). MS found: (M−H)−=204.

Aufarbeitung

  1. customPreparation H11, Step 4
  2. customTHF was removed
  3. washthe aqueous layer was washed with ether
  4. extractionThe solid product was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8471968226bd4b9fbf330bf67b7c25e6
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482335B2

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