Tetrahydrofuran → 2,3-Dihydro-6hydroxymethylimidazo[2,1-b]thiazole

HRID 992914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992914
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[S:12]1[CH2:16][CH2:15][N:14]2[CH:17]=[C:18]([C:20](OCC)=[O:21])[N:19]=[C:13]12>O>[OH:21][CH2:20][C:18]1[N:19]=[C:13]2[N:14]([CH:17]=1)[CH2:15][CH2:16][S:12]2

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 18183084Ethyl 2,3-dihydroimidazo[2,1-b]thiazole-6-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 181830822,3-Dihydro-6hydroxymethylimidazo[2,1-b]thiazoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Lithium aluminium hydride (280 mg, 7.3 mmol) was suspended in dry, redistilled THF (20 ml) under argon and treated dropwise with a solution (THF, 20 ml), of ethyl 2,3-dihydroimidazo[2,1-b]thiazole-6-carboxylate (1.32 g, 6.7 mmol). After 2 h, water was added carefully until effervescence ceased when the mixture was filtered through Celite, the filter pad washed with THF and water and the filtrate and washings combined and evaporated to dryness under reduced pressure. The residue was evaporated twice from ethanol to give the title compound as a white solid (1.03 g, 100%); dH (250 MHz; CD3OD) 3.73-3.95 (2H, m), 4.06-4.30 (2H, m), 4.42 (2H, s), 7.04 (1H, s).

Aufarbeitung

  1. customin dry
  2. distillationredistilled THF (20 ml) under argon
  3. filtrationwas filtered through Celite
  4. washthe filter pad washed with THF and water
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was evaporated twice from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-11c0cda33a804287ab8b876eaca2eee3
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06472383B1

Notizen zur Reaktion

Wird geladen…