Water → 2-(3,4-Diethoxyphenyl)-4-styrylthiazole

Temperature

-50 °C

4.2 ml of n-butyllithium was dropwise added in small portions to a suspension of 2.6 g of benzyltriphenylphosphonium chloride in 10 ml of tetrahydrofuran, with stirring at −50° C. The mixture was heated to room temperature and, after cooling again to −50° C., was mixed with 12 ml of a tetrahydrofuran solution of 2 g of 2-(3,4-diethoxyphenyl)-4-formylthiazole. The mixture was stirred at the same temperature for 30 minutes and at room temperature for 14 hours. 10 ml of water and 40 ml of ethyl acetate were added to conduct extraction and phase separation. The solvent layer was dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography to obtain 2 g of 2-(3,4-diethoxyphenyl)-4-styrylthiazole as a 1:1 mixture of cis form and trans form.

1. temperatureThe mixture was heated to room temperature
2. temperatureafter cooling again to −50° C.
3. stirringThe mixture was stirred at the same temperature for 30 minutes and at room temperature for 14 hours
4. extractionextraction and phase separation
5. customThe solvent layer was dried
6. distillationsubjected to distillation
7. customto remove the solvent
8. customThe residue was purified by silica gel column chromatography

ORD record

ord-0ae349d026204cd19d8d322ac9f9fdde

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE037556E1