Tetrahydrofuran → 1-(2,3-Dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-3-phenylprop-2-en-1-ol

HRID 635850

Reaktionsgleichung

Reaktionsgleichung von HRID 635850
[CH3:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([C:10](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[N:4]2[C:3]=1[CH3:20].C1COCC1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([CH:10]([CH:12]=[CH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[OH:11])[N:4]2[C:3]=1[CH3:20]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 212565022,3-Dimethyl-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazol-5-yl methanone

Produkt 1

HCID 4670981-(2,3-Dimethylimidazo[2,1-b][1,3]thiazol-5-yl)-3-phenylprop-2-en-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 2,3-Dimethyl-α-(2-phenyl-E-ethenyl)imidazo[2,1-b]thiazole-5-methanone (FIG. D-2) (0.34 g) in 1:1 ethanol:THF (40 mL) was treated with a solution of NaBH4 (0.35 g) in ethanol (5 mL). The solution was reacted for 2.5 hours, evaporated in vacuo, and the residue was diluted with water. The precipitated 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol (FIG. D-5) was extracted into ethyl acetate, the extract was dried and evaporated to a viscous residue. The residue was triturated with ethyl acetate to yield 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol (FIG. D-5), 0.28 g, m.p. 149-151° after crystallization from acetonitrile.

Aufarbeitung

  1. customThe solution was reacted for 2.5 hours
  2. customevaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionThe precipitated 2,3-Dimethyl-α-(2-phenylethenyl)imidazo[2,1-b]thiazole-5-methanol (FIG. D-5) was extracted into ethyl acetate
  5. customthe extract was dried
  6. customevaporated to a viscous residue
  7. customThe residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-192b789b89b84680bdc5e6522e121c9e
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06191124B1

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