4-Hydroxybenzaldehyde → 2-(4-Vinylphenoxy)ethanol

4-Hydroxybenzaldehyde (3.664 g) was dissolved in N, N-dimethylformamide (60 ml), followed by the addition of 60% sodium hydride (1.44 g) under ice-cooling. The resulting mixture was stirred at room temperature for 40 min. To the mixture was added (2-bromoethoxy)-t-butyldimethylsilane (8.612 g), and the resulting mixture was stirred at 100° C. for 30 min. After the mixture was cooled as it was, it was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was dissolved in N,N-dimethylformamide (70 ml), followed by the addition of (ethyl)triphenylphosphonium bromide (13.218 g) and 60% sodium hydride (1.623 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, extracted with hexane extraction, and then the resulting organic layer was evaporated. The resulting residue was dissolved in tetrahydrofuran (50 ml), followed by the addition of 2N hydrochloric acid (20 ml) and stirring for 1 hr. The reaction mixture was extracted with ethyl acetate, and the resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless solid (3.025 g, yield; 60%).

1. temperaturecooling
2. stirringthe resulting mixture was stirred at 100° C. for 30 min
3. temperatureAfter the mixture was cooled as it
4. customit was partitioned between ethyl acetate and water
5. washThe resulting organic layer was washed with water
6. dry with materialdried (over MgSO4)
7. customevaporated
8. dissolutionThe resulting residue was dissolved in N,N-dimethylformamide (70 ml)
9. additionfollowed by the addition of (ethyl)triphenylphosphonium bromide (13.218 g) and 60% sodium hydride (1.623 g) under ice-
10. temperaturecooling
11. stirringthe resulting mixture was stirred at room temperature for 2 hr
12. additionWater was added to the reaction mixture
13. extractionextracted with hexane extraction
14. customthe resulting organic layer was evaporated
15. dissolutionThe resulting residue was dissolved in tetrahydrofuran (50 ml)
16. additionfollowed by the addition of 2N hydrochloric acid (20 ml)
17. stirringstirring for 1 hr
18. extractionThe reaction mixture was extracted with ethyl acetate
19. washthe resulting organic layer was washed with water
20. dry with materialdried (over MgSO4)
21. customevaporated
22. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

ORD-Eintrag

ord-4f17641b2b274359b0ded572f6376565

Quelldatensatz

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06875761B2