Sodium Acetate → (E)-(2-Styryloxazol-4-yl)methanol

Temperatur

90 °C

A mixture of 4-chloromethyl-2-[(E)-2-phenylethenyl]oxazole (5.0 g), sodium acetate (7.48 g) and N,N-dimethylformamide (50 ml) was stirred at 90° C. for 4.5 hours. The reaction mixture was poured onto ice-water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water dried (MgSO4), and concentrated under reduced pressure. To the residue was added potassium carbonate (4.73 g), water (25 ml) and methanol (50 ml) and then the resultant was stirred for 2 hours at room temperature. The reaction mixture was concentrated, to which was added brine, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 2-[(E)-2-phenylethenyl]-4-oxazolylmethanol (4.18 g, 91%). Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 94-95° C.

1. additionThe reaction mixture was poured onto ice-water
2. extractionextracted with ethyl acetate
3. washThe ethyl acetate layer was washed with water
4. dry with materialdried (MgSO4)
5. concentrationconcentrated under reduced pressure
6. additionTo the residue was added potassium carbonate (4.73 g), water (25 ml) and methanol (50 ml)
7. stirringthe resultant was stirred for 2 hours at room temperature
8. concentrationThe reaction mixture was concentrated, to which
9. additionwas added brine
10. extractionextracted with ethyl acetate
11. washThe ethyl acetate layer was washed with water
12. dry with materialdried (MgSO4)
13. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-c5358636fe4f4ed4ace4be461aad04ea

Quelldatensatz

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06211215B1