Triphenylphosphine → 1-Methoxypropylthiazole

Diethyl azodicarboxylate (0.38 ml) was added dropwise to a mixture of 2-[1-(3 hydroxyphenyl)-1-methoxypropyl]thiazole (0.37 g), triphenylphosphine (0.57 g), 3-(3-pyridyl)prop-2-en-1-ol (0.27 g) and tetrahydrofuran (7 ml) which had been cooled to 0°-5° C. in an ice-bath. The mixture was stirred at this temperature range for 2 hours and then at ambient temperature for 4 hours. Further portions of diethyl azodicarboxylate (0.1 ml), triphenylphosphine (0.14 g) and the propenol (0.045 g) were added and the mixture was stirred at ambient temperature for 18 hours. The mixture was partitioned between ethyl acetate (40 ml) and dilute aqueous hydrochloric acid (40 ml). The aqueous layer was separated and basified by adding potassium carbonate portionwise. The resulting solution was extracted with ethyl acetate (3×20 ml). The combined extracts were dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with toluene/ethyl acetate (2/3 v/v) to give 2-[1-[3-(3-pyridyl)prop-2-en-1-yloxy)phenyl[-1-methoxypropylthiazole as a colourless oil (0.162 g).

1. temperaturehad been cooled to 0°-5° C. in an ice-bath
2. waitat ambient temperature for 4 hours
3. stirringthe mixture was stirred at ambient temperature for 18 hours
4. customThe mixture was partitioned between ethyl acetate (40 ml) and dilute aqueous hydrochloric acid (40 ml)
5. customThe aqueous layer was separated
6. additionby adding potassium carbonate portionwise
7. extractionThe resulting solution was extracted with ethyl acetate (3×20 ml)
8. dry with materialThe combined extracts were dried (Na2SO4)
9. customevaporated
10. customThe residue was purified by column chromatography
11. washeluting with toluene/ethyl acetate (2/3 v/v)

ORD record

ord-d942e4864a154653a4c59578476f70e2

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05089495