JOURNAL OF CHEMICAL RESEARCH 2014 75
2.71 (m, 2H), 2.32 (br s, 1H, OH); 13C NMR (100 MHz, CDCl3): 159.9,
133.1, 126.8, 117.3, 114.3, 69.9, 55.3, 27.9.
Received 16 October 2013; accepted 28 November 2013
Paper 1302236 doi: 10.3184/174751914X13888556743823
Published online: 5 February 2014
3-Hydroxy-5-phenylpent-4-enenitrile (3f): Oil,11,12,19 IR (υ/cm–1): 3398,
3019, 2236, 1529; 1H NMR (400 MHz, CDCl3, TMS): 7.57–7.25 (m, 5H),
6.72–6.84 (d, 1H), 6.26–6.20 (t, 1H), 4.64–4.60(q, J=5.6 Hz, 1H), 2.73–
2.61 (m, 2H), 2.51(br s, 1H, OH); 13C NMR (100 MHz, CDCl3): 135.5,
132.9, 128.7, 128.4, 127.9, 126.7, 117.2, 68.6, 26.3.
References
1
2
3
4
5
6
E.J. Corey and Y.J. Wu, J. Am. Chem. Soc., 1993, 115, 8871.
F. Fleming and B.C. Shook, Tetrahedron, 2002, 58, 1.
Y. Fukuda and Y. Okamoto, Tetrahedron, 2002, 58, 2513.
N.S. Li, S. Yu and G.W. Kabalka, J. Org. Chem., 1995, 60, 5973.
Y. Kawano, N. Kaneko and T. Mukaiyama, Chem. Lett., 2005, 34, 1508.
S. Choppin, L.F. Medeiros, M. Barbarottoa and F. Colobert, Chem. Soc.
Rev., 2013, 42, 937.
3-Hydroxy-4-methyl-5-phenylpent-4-enenitrile (3g): Oil, IR (υ/cm–1):
1
3402, 3014, 2238, 1526; H NMR (400 MHz, CDCl3, TMS): 7.37–7.23
(m, 5H), 6.64 (s, 1H), 4.54–4.53(t, J=6.0 Hz, 1H), 2.70–2.67 (q, 2H),
2.48 (br s, 1H, OH), 1.88 (s, 3H); 13C NMR (100 MHz, CDCl3): 136.6,
136.4, 128.9, 128.2, 127.6, 127.0, 117.4, 73.2, 24.6, 13.2; HRMS calcd for
C12H13N O[M+H]+: 188.1075, found: 188.1079.
3-(Furan-2-yl)-3-hydroxypropanenitrile (3h): Oil,19 IR (υ/cm–1): 3405,
2236, 1612, 1518, 1H NMR (400 MHz, CDCl3, TMS): 7.42–7.40(m, 1H),
6.39–6.36 (m, 2H), 5.05–5.02 (t, J=6.0 Hz, 1H), 3.13 (br s, 1H, OH),
2.91–2.88 (m, 2H), 13C NMR (100 MHz, CDCl3): 152.8, 142.8, 116.9,
110.5, 107.4, 63.7, 24.8.
7
8
9
P.G. Cozzi, Angew. Chem. Int. Ed., 2007, 46, 2568.
R. Ocampo and W.R. Jr. Dolbier, Tetrahedron, 2004, 60, 9325.
S. Inaba and R.D. Rieke, Tetrahedron Lett., 1985, 26, 155.
10 Z.L. Zhou, L.L. Shi and Y.Z. Huang, J. Chem. Soc. Perkin Trans., 1991, 1,
1931.
11 P.P. Sun and B.C. Shi, J. Chem. Res., 1999, 318.
12 S. Araki, M. Yamada and Y. Butsugan, Bull. Chem. Soc. Jpn, 1994, 67,
1126.
13 A. Caracoti and R.A. Flowers, Tetrahedron Lett., 2000, 41, 3039.
14 N.A. Ross, R.A. Bartsch and A.P. Marchand, Tetrahedron, 2004, 60, 2035.
15 N.A. Ross and R.A. Bartsch, J. Org. Chem., 2003, 68, 360.
16 A.R. Gholap and A.P. Chavan, J. Chem. Res., 2003, 374.
17 Y.M. Zhang, X.F. Jia and J.-X. Wang, Eur. J. Org. Chem., 2009, 2983.
18 P. Knochel, M.C.P. Yeh, S.C. Berk and J. Talbert, J. Org. Chem., 1988, 53,
2390.
3-Hydroxy-3-phenylbutanenitrile (3i): Oil,12 IR (υ/cm–1): 3408, 3027,
2249, 1516; 1H NMR (400 MHz, CDCl3, TMS): 7.49–7.26 (m, 5H),
2.87–2.77 (q, 2H), 2.42 (br s, 1H, OH), 1.76 (s, 3H); 13C NMR (100 MHz,
CDCl3): 144.5, 128.7, 127.9, 117.3, 72.4, 33.6, 29.1.
This work was supported by ‘Qing Lan’ Talent Engineering
Funds of Lanzhou Jiaotong University.
19 Y.C. Fan, G.F. Du, W.F. Sun, W. Kang and L. He, Tetrahedron Lett., 2012,
53, 2231.
JCR1302236_FINAL.indd 75
30/01/2014 11:32:52