* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Journal of the American Chemical Society, 1984, vol. 106, # 11, p. 3344 - 3353
[2] J. Gen. Chem. USSR (Engl. Transl.), 1987, vol. 57, p. 1366 - 1371[3] Zhurnal Obshchei Khimii, 1987, vol. 57, # 7, p. 1534 - 1540
[4] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7764 - 7769
2
[ 107-14-2 ]
[ 603-35-0 ]
[ 4336-70-3 ]
Yield
Reaction Conditions
Operation in experiment
49.58%
for 6 h; Reflux
chloroacetonitrile (10 g, 0.132 mol) was added dropwise to a solution of triphenylphosphine (23.5g, 0.0895 mol) in (120 mL) toluene and heated at reflux for 6 h. The reaction mixture was cooled to room temperature, the solids filtered and washed with (2 x 20 mL) diethyl ether. Compound (15 g, 49.58percent) was obtained as a white solid. -NMR (400 MHz, DMSO) δ 8.02-7.97 (m, 3H), 7.90-7.79 (m, 12H), 5.94 (s, 1 H), 5.90 (s, 1H); LC-MS (ES, m/z): [M+H]+= 301.7
49.58%
for 6 h; Reflux
chloroacetonitrile (10 g, 0.132 mol) was added dropwise to a solution of triphenylphosphine (23.5 g, 0.0895 mol) in(120 mL) toluene and refluxed for 6 h. The reaction mixture was cooled to room temperature and the solids were filtered and washed with (2 x 20 mL) diethyl ether to give the product (15 g, 49.58percent) as a white solid. ‘H-NMR (400 MHz, DMSO) ö 8.02-7.97 (m, 3H), 7.90-7.79 (m, 12H), 5.94 (s, 1H), 5.90 (s, 1H); LCMS [M+Hf’ 301.7.
49.58%
for 6 h; Reflux
chioroacetonitrile (10 g, 0.132 mol) was added dropwise to a solution of triphenylphosphine (23.5g, 0.0895 mol) in (120mL) toluene and heated at reflux for 6 h. The reaction mixture was cooled to room temperature, the solids filtered and washed with (2 x 20 mL) diethyl ether. Compound (15 g, 49.5 8percent) was obtained as a white solid. ‘H-NMR (400 MHz, DMSO) ö 8.02-7.97 (m, 3H),7.90-7.79 (m, 12H), 5.94 (s, 1H), 5.90 (s, 1H); LC-MS (ES, m/z): [M+Hf’= 301.7
Reference:
[1] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 132 - 138
[2] Chemistry - A European Journal, 2013, vol. 19, # 7, p. 2442 - 2449
[3] Journal of Organic Chemistry, 1980, vol. 45, # 26, p. 5316 - 5319
[4] International Journal of Chemical Kinetics, 2006, vol. 38, # 8, p. 496 - 502
[5] Patent: WO2016/105485, 2016, A2, . Location in patent: Paragraph 0158
[6] Patent: WO2017/19589, 2017, A1, . Location in patent: Paragraph 0133
[7] Patent: WO2017/112853, 2017, A1, . Location in patent: Paragraph 0133
[8] Tetrahedron, 1997, vol. 53, # 31, p. 10677 - 10688
[9] Tetrahedron, 2005, vol. 61, # 11, p. 2779 - 2794
[10] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 3, p. 764 - 772
3
[ 545-06-2 ]
[ 603-35-0 ]
[ 4336-70-3 ]
Reference:
[1] J. Gen. Chem. USSR (Engl. Transl.), 1979, vol. 49, p. 889 - 894[2] Zhurnal Obshchei Khimii, 1979, vol. 49, p. 1025 - 1031
[3] Journal of the American Chemical Society, 1965, vol. 87, # 22, p. 5068 - 5075
4
[ 1120-06-5 ]
[ 1002-56-8 ]
[ 20063-97-2 ]
[ 4336-70-3 ]
Reference:
[1] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 8.1, p. 1409 - 1415[2] Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 8, p. 1611 - 1618
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 0.5h;Heating / reflux;
3-FURALDEHYDE (0.43 mL, 5 mM), (cyanomethyl) triphenylphosphonium chloride (1.77 g, 5.3 mmol), DBU (0.82 mL, 5.5 mmol) in toluene (50 mL) were heated at reflux for 30 min, then the reaction volume was reduced in vacuo and the entire reaction contents added to a silica gel column. Elution with 15 % ethyl ACETATE/HEXANES gave 3-furan-3-yl-acrylonitrile (quant) as a 5: 1 mixture ('H NMR) of the E/Z isomers.