Dimethylformamide → 4-(Hydroxymethyl)-2-phenyl-1,3-thiazole

Temperatur

80 °C

A mixture of 4-chloromethyl-2-phenylthiazole (8.60 g), sodium acetate (10.1 g) and N,N-dimethylformamide (80 ml) was stirred at 80° C. for 6 hours. After cooling, the reaction solution was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. A mixture of the residue, 4N aqueous sodium hydroxide solution (25 ml), tetrahydrofuran (50 ml) and methanol (50 ml) was stirred at room temperature for 5 minutes, and poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 2-phenyl-4-thiazolylmethanol (7.05 g, yield 90%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). This was recrystallized from hexane. Melting point: 71–72° C.

1. temperatureAfter cooling
2. extractionwas extracted with ethyl acetate
3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
4. dry with materialdried (MgSO4)
5. concentrationconcentrated
6. additionA mixture of the residue, 4N aqueous sodium hydroxide solution (25 ml), tetrahydrofuran (50 ml) and methanol (50 ml)
7. stirringwas stirred at room temperature for 5 minutes
8. additionpoured into water, which
9. extractionwas extracted with ethyl acetate
10. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
11. dry with materialdried (MgSO4)
12. concentrationconcentrated

ORD-Eintrag

ord-71a985ac0d894521b3aa3f651762407b

Quelldatensatz

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07179823B1