Tetrapropylammonium → HCID 21941485、化合物

To a solution of 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarbaldehyde (1.02 g, 6.07 mmol) in THF (30 ml) was added 6.68 ml of a 1.0 M solution of tetrabutylammonium fluoride in THF at 0° C. After stirring for 1 hr, the mixture was treated with 10 ml of saturated ammonium chloride solution and extracted with ethyl acetate. The organic solution was washed with brine, dried over anhydrous sodium sulfate, filtered through Magnesol and evaporated. The crude gum was washed with hexanes, dried in vacuo, and then dissolved in methylene chloride (20 ml). To this solution was added 4-methylmorpholine-N-oxide (2.89 g, 24 mmol) and molecular sieve 4A (6 g). The mixture was stirred at room temperature for 10 min. and then treated with tetrapropylammonium peruthenate (0.11 g, 0.3 mmol). Stirring was continued for 2 hr. The methylene chloride solution was concentrated and diluted with ethyl acetate (40 ml). The mixture was filtered through a pad of silica gel (40 g) and the filter pad was eluted with 2×20 ml ethyl acetate. The combined eluent was washed with 1N HCl and brine, dried over anhydrous sodium sulfate, and evaporated to give 0.30 g of a white solid; mp 135–136° C.; MS m/e 167 (MH+).

1. extractionextracted with ethyl acetate
2. washThe organic solution was washed with brine
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered through Magnesol
5. customevaporated
6. washThe crude gum was washed with hexanes
7. customdried in vacuo
8. dissolutiondissolved in methylene chloride (20 ml)
9. stirringThe mixture was stirred at room temperature for 10 min.
10. stirringStirring
11. waitwas continued for 2 hr
12. concentrationThe methylene chloride solution was concentrated
13. additiondiluted with ethyl acetate (40 ml)
14. filtrationThe mixture was filtered through a pad of silica gel (40 g)
15. washthe filter pad was eluted with 2×20 ml ethyl acetate
16. washThe combined eluent was washed with 1N HCl and brine
17. dry with materialdried over anhydrous sodium sulfate
18. customevaporated

ORDレコード

ord-431a4d5169f040f9ae94dd10bd53325d

出典データセット

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07112582B2