![](/CAS/GIF/399-06-4.gif)
4,4,4-Trifluoro-1-(pyridine-4-yl)butane-1,3-dione synthesis
- Product Name:4,4,4-Trifluoro-1-(pyridine-4-yl)butane-1,3-dione
- CAS Number:399-06-4
- Molecular formula:C9H6F3NO2
- Molecular Weight:217.14
![4-Acetylpyridine](/CAS/GIF/1122-54-9.gif)
1122-54-9
412 suppliers
$10.00/5G
![Ethyl trifluoroacetate](/CAS/GIF/383-63-1.gif)
383-63-1
474 suppliers
$10.00/25g
![Sodium Methoxide](/CAS/GIF/124-41-4.gif)
124-41-4
681 suppliers
$12.00/25g
![4,4,4-Trifluoro-1-(pyridine-4-yl)butane-1,3-dione](/CAS/GIF/399-06-4.gif)
399-06-4
41 suppliers
$80.00/1g
Yield:399-06-4 62%
Reaction Conditions:
with citric acid in methanol;tert-butyl methyl ether at 20; for 22 h;
Steps:
40 4.1.40 4-Trifluoroacetoacetylpyridine (17)
To a solution of ethyl trifluoroacetate (6.32 g, 44.5 mmol) and a 28% sodium methoxide-methanol solution (9.4 g, 49 mmol) in tert-butyl methyl ether (10 mL) was added a solution of 4-acetylpyridine (16, 4.90 g, 40.4 mmol) in tert-butyl methyl ether (20 mL) at room temperature and the mixture was stirred for 22 h.
A 10% citric acid aqueous solution was added until the reaction solution became about pH 4.
The precipitate was collected by filtration, washed with water and dried to give the title compound (5.46 g, 62%) as a yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 6.60 (1H, br s), 7.96 (2H, d, J = 5.5 Hz), 8.82 (2H, d, J = 5.5 Hz).
References:
Yoshida, Tomohiro;Akahoshi, Fumihiko;Sakashita, Hiroshi;Kitajima, Hiroshi;Nakamura, Mitsuharu;Sonda, Shuji;Takeuchi, Masahiro;Tanaka, Yoshihito;Ueda, Naoko;Sekiguchi, Sumie;Ishige, Takayuki;Shima, Kyoko;Nabeno, Mika;Abe, Yuji;Anabuki, Jun;Soejima, Aki;Yoshida, Kumiko;Takashina, Yoko;Ishii, Shinichi;Kiuchi, Satoko;Fukuda, Sayaka;Tsutsumiuchi, Reiko;Kosaka, Keigo;Murozono, Takahiro;Nakamaru, Yoshinobu;Utsumi, Hiroyuki;Masutomi, Naoya;Kishida, Hiroyuki;Miyaguchi, Ikuko;Hayashi, Yoshiharu [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 19,p. 5705 - 5719]