4-NONENAL (TRANS) synthesis
- Product Name:4-NONENAL (TRANS)
- CAS Number:2277-16-9
- Molecular formula:C9H16O
- Molecular Weight:140.22
69361-38-2
1 suppliers
inquiry
2277-16-9
5 suppliers
inquiry
Yield: 91%
Reaction Conditions:
with diisobutylaluminium hydride in diethyl ether;hexane at -78; for 1 h;Inert atmosphere;
Steps:
(E)-Non-4-enal (11).
To a stirred solution of 10 (10.0 g, 54.3 mmol) in Et2O (270 mL) was added dropwise a solution of DIBAL (1.0 M in hexane, 60.0 mL, 60 mmol, 1.1 eq) at -78 °C under N2. After 1 h of stirring, the reaction was quenched by slow addition of EtOAc at -78 °C and then warmed to ambient temperature. To the mixture was added satd aq Rochelle’s salt and the resulting mixture was stirred vigorously for 3 h. After extraction of the mixture with Et2O (3 times)the extract was successively washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 column chromatography (hexane/EtOAc = 9:1) to give aldehyde 11 (6.9 g, 91 %) as a colorless oil. IR: νmax 3021 (w), 2718 (m), 1729 (vs), 969 (s); 1H NMR: δ 0.88 (3H, t, J = 7.0 Hz), 1.23-1.37 (4H, m), 1.98 (2H, br q, J = 6.6 Hz ), 2.33 (2H, q, J = 6.8 Hz), 2.46-2.52 (2H, m), 5.39 (1H, dt, J = 15.6, 6.0 Hz), 5.47 (1H, dt, J = 15.6, 6.4 Hz), 9.76 (1H, t, J = 1.8 Hz); 13C NMR: δ 13.9, 22.2, 25.2, 31.6, 32.1, 43.6, 127.6, 132.1, 202.4; HRMS (EI): m/z calcd for C9H16O, 140.1201; found, 140.1200 ([M]+).
References:
Fujishima, Yuki;Ogura, Yusuke;Towada, Ryo;Enomoto, Masaru;Kuwahara, Shigefumi [Tetrahedron Letters,2016,vol. 57,# 47,p. 5240 - 5242] Location in patent:supporting information
16695-34-4
3 suppliers
inquiry
2277-16-9
5 suppliers
inquiry
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
0 suppliers
inquiry
2277-16-9
5 suppliers
inquiry
