1278
J.-M. Vatèle
LETTER
(
6) (a) Bailey, A.; James, B. B. Chem. Commun. 1996, 2343.
b) Mori, K.; Yamaguchi, T.; Mizugaki, T.; Ebitani, K.;
(Na SO ), filtered, and evaporated under reduced pressure.
The residue was purified by flash column chromatography
2
4
(
Kaneda, K. Chem. Commun. 2001, 461. (c) Yamaguchi, K.;
Mizuno, N. Angew. Chem. Int. Ed. 2003, 42, 1480.
(PE–Et O or PE–CH Cl ) to give 2.
(Trityloxy)pentanenitrile (2d):
2
2
2
(
d) Kotani, M.; Koike, T.; Yamaguchi, K.; Mizuno, N.
Eluent: PE–Et O (95:5). Yield: 92%; solid; mp 72–74 °C
2
1
Green Chem. 2006, 8, 735. (e) Reddy, K. R.; Maheswari, C.
U.; Venkateshwar, M.; Prashanti, S.; Kantam, M. L.
Tetrahedron Lett. 2009, 50, 2050. (f) Zhang, Y.; Xu, K.;
Chen, X.; Hu, T.; Yu, Y.; Zhang, J.; Hung, J. Catal.
Commun. 2010, 11, 951. (g) Zhu, C.; Sun, C.; Wei, Y.
Synthesis 2010, 4235. (h) Kim, J.; Stahl, S. S. ACS Catal.
(hexane). H NMR (300 MHz, C D ): δ = 7.56–7.46 (m,
6
6
6 H), 7.22–7.11 (m, 6 H), 7.11–7.02 (m, 3 H), 2.92 (t,
J = 6.1 Hz, 2 H), 1.41 (t, J = 7.1 Hz, 2 H), 1.37–1.28 (m,
1
3
2 H), 1.17–1.06 (m, 2 H). C NMR (75 MHz, C D ): δ =
6
6
144.7 (3C), 129.0 (6C), 128.1 (6C), 127.3 (3C), 119.3, 86.9,
+
62.6, 29.0, 22.6, 16.5. HRMS (ESI): m/z [M + Na] calcd for
2
013, 3, 1652.
C H NNaO: 364.1672; found: 364.1663.
2
4
23
(
7) (a) Erman, M. B.; Snow, J. W.; Williams, M. J. Tetrahedron
Lett. 2000, 41, 6749. (b) Lai, G.; Bhamare, N. K.; Anderson,
W. K. Synlett 2001, 230. (c) Talukdar, S.; Hsu, J. L.; Tchu,
T. C.; Fang, J. M. Tetrahedron Lett. 2001, 42, 1103.
5-[(tert-Butyldimethylsilyl)oxy]pentanenitrile (2e):
1
Eluent: PE–Et O (9:1); Yield: 97%; liquid. H NMR (300
2
MHz, C D ): δ = 3.27 (t, J = 5.7 Hz, 2 H), 1.54 (t,
6
6
J = 6.7 Hz, 2 H), 1.32–1.06 (m, 4 H), 0.91 (m, 9 H), –0.02
13
(
(
d) Bandgar, B. P.; Makone, S. S. Synlett 2003, 262.
e) Carmeli, M.; Shefer, N.; Rozen, S. Tetrahedron Lett.
(m, 6 H). C NMR (75 MHz, C D ): δ = 119.4, 62.0, 31.6,
6 6
26.1 (3 C), 22.4, 18.4, 16.5, –5.3 (2 C). HRMS (ESI): m/z [M
+
2
006, 47, 8969. (f) Arote, N. D.; Bhalerao, D. S.;
Akamanchi, K. G. Tetrahedron Lett. 2007, 48, 3651.
g) Telvekar, V. N.; Patel, K. N.; Kundaikar, H. S.;
+ Na] calcd for C H NNaOSi: 236.1441; found:
1
1
23
236.1435.
(Z)-4-(Benzyloxy)but-2-enenitrile (2r):
(
1
Chaudari, H. K. Tetrahedron Lett. 2008, 49, 2213. (h) Bag,
S.; Tawari, N. R.; Degani, M. S. ARKIVOC 2009, (xiv), 118.
Eluent: PE–Et O (4:1). Yield: 92%; liquid. H NMR (300
2
MHz, C D ): δ = 7.22–7.02 (m, 5 H), 5.82 (dt, J = 11.3,
6
6
(
(
i) Zhu, Y.-Z.; Cai, C. Monatsh. Chem. 2010, 141, 637.
j) Telvekar, V. N.; Rane, R. A.; Namjoshi, T. V. Synth.
6.0 Hz, 1 H), 4.56 (dt, J = 11.3, 1.8 Hz, 1 H), 4.10 (s, 2 H),
1
3
3.86 (dd, J = 6.0, 1.8 Hz, 2 H). C NMR (75 MHz, C D ): δ
6
6
Commun. 2010, 40, 494. (k) Zhu, Y.-Z.; Zhang, X.-Q.; Liu,
F.; Gu, H.-M.; Zhu, H.-L. Synth. Commun. 2013, 43, 2943.
8) (a) Yamazaki, S.; Yamazaki, Y. Chem. Lett. 1990, 571.
= 150.2, 138.1, 128.6 (2 C), 128.0, 127.97 (2 C), 115.3,
100.3, 72.9, 68.2. HRMS (ESI): m/z [M + Na] calcd for
+
(
C H NNaO: 196.0733; found: 196.0731.
1
1
11
(
b) McAllister, G. D.; Wilfried, C. D.; Taylor, R. J. K.
10-Hydroxyundecanenitrile (2t):
1
Synlett 2002, 1291. (c) Chen, F.-E.; Li, Y.-Y.; Xu, M.; Jia,
H.-Q. Synthesis 2002, 1804. (d) Togo, H.; Iida, S.
Eluent: PE–Et O (1:2). Yield: 84%; liquid. H NMR (300
2
MHz, CDCl ): δ = 3.79–3.64 (m, 1 H), 2.28 (t, J = 7.1 Hz,
3
Tetrahedron 2007, 63, 8274. (e) Oishi, T.; Yamaguchi, K.;
Mizuno, N. Angew. Chem. Int. Ed. 2009, 48, 6286. (f) Oishi,
T.; Yamaguchi, K.; Mizuno, N. Top. Catal. 2010, 53, 479.
2 H), 2.11 (s, 1 H), 1.64–1.53 (m, 2 H), 1.45–1.18 (m, 12 H),
13
1.12 (d, J = 6.2 Hz, 3 H). C NMR (75 MHz, CDCl ): δ =
3
119.7, 67.7, 39.0, 29.2, 29.0, 28.44, 28.38, 25.45, 25.1, 23.2,
+
(
g) Veisi, N. Synthesis 2010, 2631. (h) Zolfigol, M. A.;
16.9. HRMS (ESI): m/z [M + Na] calcd for C H NNaO:
1
1
21
Hajjami, M.; Ghorbani-Choghamarani, A. Bull. Korean
Chem. Soc. 2011, 32, 4191. (i) Ghorbani-Choghamarani, A.;
Zolfigol, M. A.; Hajjami, M.; Sardari, S. Synth. Commun.
206.1515; found: 206.1510.
10-Oxoundecanenitrile (2t′):
1
Eluent: PE–Et O (1:2). Yield 8%; liquid. H NMR (400
2
2
2
013, 43, 52. (j) Yin, W.; Wang, C.; Huang, Y. Org. Lett.
013, 15, 1850. (k) Dornan, L. M.; Cao, Q.; Flanagan, J. C.
MHz, CDCl ): δ = 2.41 (t, J = 7.4 Hz, 2 H), 2.36–2.28 (m,
2 H), 2.12 (s, 3 H), 1.73–1.12 (m, 12 H). C NMR (101
3
1
3
A.; Crawford, J. J.; Cook, M. J.; Muldoon, M. J. J. Chem.
Soc., Chem. Commun. 2013, 49, 6030. (l) Tao, C.; Liu, F.;
Zhu, Y.; Liu, W.; Cao, Z. Org. Biomol. Chem. 2013, 11,
MHz, CDCl ): δ = 209.1, 119.75, 43.6, 29.8, 29.0, 28.9, 28.5
(2 C), 25.3, 23.6, 17.05. HRMS (ESI): m/z [M + Na] calcd
3
+
for C H NNaO: 204.1359; found: 204.1355.
1
1
19
3
2
349. (m) Shimojo, H.; Moriyama, K.; Togo, H. Synthesis
013, 45, 2155.
3-Hydroxy-2,2,4-trimethylpentanenitrile (2u):
1
Eluent: PE–Et O (1.5:1). Yield: 87%; oil. H NMR (300
2
(
9) (a) Ren, Y.-M.; Zhu, Y.-Z.; Cai, C. J. Chem. Res. 2008, 18.
b) Yadav, D. K. T.; Bhanage, B. M. Eur. J. Org. Chem.
013, 5106.
10) (a) Vatèle, J.-M. Tetrahedron Lett. 2006, 47, 715.
b) Vatèle, J.-M. Synlett 2006, 2055. (c) Vatèle, J.-M.
Synlett 2008, 1785. (d) Vatèle, J.-M. Synlett 2009, 2143.
e) Vatèle, J.-M. Tetrahedron 2010, 66, 904. (f) Barnych,
MHz, CDCl ): δ = 3.20 (d, J = 3.2 Hz, 1 H), 2.44 (s, 1 H),
3
(
2
2.04–1.9 (m, 1 H), 1.39 (s, 3 H), 1.30 (s, 3 H), 1.02 (s, 3 H),
1
3
1.00 (s, 3 H). C NMR (75 MHz, CDCl ): δ = 124.3, 79.9,
3
(
37.0, 29.9, 24.7, 23.7, 21.6, 15.4. HRMS (ESI): m/z [M +
+
(
Na] calcd for C H NNaO: 164.1046; found: 164.1039.
8
15
Methyl 2,3-Di-O-benzyl-α-D-glucopyranosiduronitrile
(
(2v):
2
0
B.; Vatèle, J.-M. Synlett 2011, 2048.
Eluent: PE–Et O (2:1). Yield: 77%; glass; [α] +76.4 (c
1.3, MeOH). H NMR (300 MHz, CDCl ): δ = 7.43–7.30 (m,
2
D
1
(
11) All known compounds have physical data in accordance
with those described in the literature.
12) Oxidative Conversion of Alcohols into Nitriles; General
Procedure: To a solution of alcohol (1 mmol) in MeCN–
3
10 H), 4.93 (d, J = 11.3 Hz, 1 H), 4.79 (d, J = 7.7 Hz, 1 H),
4.75 (d, J = 7.0 Hz, 1 H), 4.64 (d, J = 11.6 Hz, 1 H), 4.60 (d,
J = 3.3 Hz, 1 H), 4.36 (d, J = 9.1 Hz, 1 H), 3.74 (t,
(
H O (9:1, 3 mL) were successively added TEMPO (7.8 mg,
J = 8.6 Hz, 1 H), 3.67 (t, J = 8.9 Hz, 1 H), 3.48 (dd, J = 3.4,
9 Hz, 1 H), 3.43 (s, 3 H), 3.10 (br s, 1 H). C NMR (75
2
1
3
5
mol%), NH OAc (0.308 g, 4 equiv), and PhI(OAc) (0.708
4
2
g, 2.2 equiv). The suspension was stirred at room
MHz, CDCl ): δ = 138.0, 137.45, 128.53 (2 C), 128.50 (2 C),
3
temperature (progress of the reaction was monitored by
TLC) for the reaction time indicated in Table 2. The resultant
clear two-phase reaction mixture was concentrated, diluted
with H O and Et O, and the organic layer was dried
128.1 (1 C), 128.03 (2 C), 127.94 (1 C), 127.91 (2 C), 116.8,
98.8, 79.7, 78.2, 75.45, 73.6, 71.35, 61.6, 56.25. HRMS
+
(ESI): m/z [M + Na] calcd for C H NNaO : 392.1468;
2
1
23
5
found: 392.1457.
2
2
Synlett 2014, 25, 1275–1278
© Georg Thieme Verlag Stuttgart · New York