S.T. Kadam, S.S. Kim / Tetrahedron 65 (2009) 6330–6334
6333
4. Experimental section
4.1. General
4.2.8. Cyano(4-nitrophenyl)methyl acetate (entry 8)
1H NMR (CDCl3, 200 MHz): 2.15 (s, 3H), 6.50 (s, 1H), 7.74 (d,
J¼11 Hz, 2H), 8.30 (d, J¼11 Hz, 2H). 13C NMR (CDCl3, 400 MHz):
20.3, 61.7, 115.1, 123.8, 124.4, 128.8, 138.1, 168.6.
In all cases the 1H NMR (200 MHz) spectra were recorded with
Varian Gemini 2000 spectrometer. Chemical shifts are reported in
ppm in CDCl3 with tetramethylsilane as an internal standard. 13C
NMR data were collected on a Varian Gemini 2000 spectrometer
(100 MHz). GC–MS were recorded with 1200L Single Quadrupole
GC/MS System with 3800GC/Varian.
4.2.9. (4-Chlorophenyl)(cyano)methyl acetate (entry 9)
1H NMR (CDCl3, 200 MHz): 2.16 (s, 3H), 6.37 (s, 1H), 7.74 (d,
J¼8 Hz, 2H), 8.42 (d, J¼8 Hz, 2H). 13C NMR (CDCl3, 400 MHz): 20.4,
61.1, 115.8, 122.2, 129.5, 130.2, 136.6, 168.6.
4.2.10. (3-Chlorophenyl)(cyano)methyl acetate (entry 10)
1H NMR (CDCl3, 200 MHz): 2.16 (s, 3H), 6.38 (s, 1H), 7.44–7.39
(m, 3H), 7.51 (s, 1H). 13C NMR (CDCl3, 400 MHz): 20.3, 62.0, 115.7,
125.9, 127.8, 130.5, 130.5, 133.6 135.0, 168.8.
4.2. General procedure for the synthesis of
O-acetylcyanohydrin
To a mixture of aldehyde (1 mmol) and TMSCN (1.2 mmol),
B(C6F5)3 (1 mol %) and Ac2O (2 mmol) were added at rt. The com-
pletion of the reaction was monitored with TLC. After the com-
pletion of reaction, the reaction mixture was filtered and
concentrated. The viscous mass was subjected to silica gel flash
column chromatography to obtain the pure compound.
1H and 13C NMR data for known products are given below which
is same with literature values.4a,c,e,8 HRMS values for new products
are given (entries 6, 7, 21–23).
4.2.11. 2-Chlorophenyl(cyano)methyl acetate (entry 11)
1H NMR (CDCl3, 200 MHz): 2.19 (s, 3H), 6.71 (s, 1H), 7.45–7.36
(m, 3H), 7.75–7.70 (m, 1H). 13C NMR (CDCl3, 400 MHz): 20.2, 60.2,
115.3, 127.6, 129.4, 130.2, 131.75, 133.4, 168.6.
4.2.12. Cyano(3-phenoxyphenyl)methyl acetate (entry 12)
1H NMR (CDCl3, 200 MHz): 2.14 (s, 3H), 6.34 (s, 1H), 7.05–7.01
(m, 3H), 7.16–7.13 (m, 2H), 7.40–7.34 (m, 4H). 13C NMR (CDCl3,
400 MHz): 20.4, 62.5, 116.0, 117.7, 119.4, 120.11, 122.2, 124.1, 130.0,
130.7, 133.6, 156.2, 158.1, 168.9. HRMS-EIþ: m/z Calcd for
C16H13NO3: 267.0895; found: 267.0899.
4.2.1. Cyano(phenyl)methyl acetate (entry 1)
1H NMR (CDCl3, 200 MHz): 2.16 (s, 3H), 6.40 (s, 1H), 7.43–7.51
(m, 5H). 13C NMR (CDCl3, 400 MHz): 20.46, 62.86, 116.20, 127.88,
129.27, 130.42, 131.68, 168.96.
4.2.13. Cyano(naphthalen-1-yl)methyl acetate (entry 13)
1H NMR (CDCl3, 200 MHz): 2.16 (s, 3H), 7.04 (s, 1H), 7.65–7.48
(m, 4H), 7.82 (d, J¼7.6 Hz, 1H), 7.93 (q, J¼8 Hz, 2H), 8.01 (d, J¼8 Hz,
1H). 13C NMR (CDCl3, 400 MHz): 20.4, 61.3, 116.2, 122.6, 125.1, 126.6,
127.0, 127.6, 127.7, 129.2, 130.0, 131.5, 133.9, 169.1.
4.2.2. Cyano(phenyl)methyl benzoate (entry 2)
1H NMR (CDCl3, 200 MHz): 6.66 (s, 1H), 7.40–7.66 (m, 5H),
8.17–8.03 (m, 5H). 13C NMR (CDCl3, 400 MHz): 63.3, 116.2, 127.9,
128.1, 128.7, 128.9, 129.3, 130.1, 130.4, 130.5, 131.8, 134.1, 134.6,
164.6. HRMS-EIþ: m/z Calcd for C15H11NO2: 237.0790; found:
237.0787.
4.2.14. (E)-1-Cyano-3-phenylallyl acetate (entry 14)
1H NMR (CDCl3, 200 MHz): 2.16 (s, 3H), 6.03 (d, J¼7.2 Hz, 1H),
6.20 (dd, J¼16.4, 7.2 Hz, 1H), 6.98 (d, J¼16 Hz, 1H), 7.42–7.33 (m,
5H). 13C NMR (CDCl3, 400 MHz): 20.4, 61.5, 118.4, 127.2, 128.8, 129.4,
134.4, 137.7, 168.9.
4.2.3. Cyano(4-methoxyphenyl)methyl acetate (entry 3)
1H NMR (CDCl3, 200 MHz): 2.12 (s, 3H), 3.81 (s, 3H), 6.34 (s, 1H),
7.92 (d, J¼6 Hz, 2H), 7.45 (d, J¼8 Hz, 2H). 13C NMR (CDCl3,
400 MHz): 20.46, 55.41, 62.62, 114.56, 116.47, 123.86, 129.66, 161.13,
169.07.
4.2.15. 1-Cyano-3-phenylpropyl acetate (entry 15)
1H NMR (CDCl3, 200 MHz): 2.10 (s, 3H), 2.20 (q, J¼13 Hz, 2H),
2.81 (t, J¼8.6 Hz, 2H), 5.25 (t, J¼6.8 Hz, 1H), 7.32–7.16 (m, 5H). 13C
NMR (CDCl3, 400 MHz): 20.3, 30.7, 33.7, 60.5, 116.8, 126.7, 128.3,
128.8, 139.1, 168.1.
4.2.4. Cyano(p-tolyl)methyl acetate (entry 4)
1H NMR (CDCl3, 200 MHz): 2.15 (s, 3H), 2.38 (s, 3H), 6.36 (s, 1H),
7.25 (d, J¼8 Hz, 2H), 7.36 (d, J¼8 Hz, 2H). 13C NMR (CDCl3,
400 MHz): 20.4, 21.2, 62.7, 116.3, 127.9, 128.9, 129.9, 140.6, 169.0.
4.2.16. Cyano(cyclohex-3-enyl)methyl acetate (entry 16)
1H NMR (CDCl3, 200 MHz): 1.51–1.48 (m, 2H), 2.05–1.93 (m, 4H),
2.15 (s, 3H), 2.20–2.16 (m, 2H), 5.25 (d, J¼8 Hz, 1H), 5.73–5.64 (m,
2H). 13C NMR (CDCl3, 400 MHz): 20.3, 23.9, 24.2, 26.6, 36.3, 64.9,
116.3, 124.3, 127.1, 170.9.
4.2.5. Cyano(m-tolyl)methyl acetate (entry 5)
1H NMR (CDCl3, 200 MHz): 2.15 (s, 3H), 2.32 (s, 3H), 6.37 (s, 1H),
7.34–7.25 (m, 4H). 13C NMR (CDCl3, 400 MHz): 20.4, 21.3, 62.9,116.2,
124.9, 128.4, 129.1, 131.1, 131.6, 139.2, 168.9.
4.2.17. Cyano(furan-2-yl)methyl acetate (entry 17)
4.2.6. Cyano(4-methoxy-3-methylphenyl)methyl
acetate (entry 6)
1H NMR (CDCl3, 200 MHz): 2.21 (s, 3H), 6.48 (s, 1H), 6.83 (d,
J¼4 Hz, 1H), 7.18 (d, J¼3.6 Hz, 1H), 7.25 (d, J¼2 Hz, 1H). 13C NMR
(CDCl3, 400 MHz): 20.2, 70.2, 113.4, 114.1, 142.2, 154.3, 169.6.
1H NMR (CDCl3, 200 MHz): 2.13 (s, 3H), 2.23 (s, 3H), 3.84 (s, 3H),
6.31 (s, 1H), 6.84 (d, J¼8.4 Hz, 1H), 7.32 (d, J¼10 Hz, 2H). 13C NMR
(CDCl3, 400 MHz): 16.1, 20.4, 55.4, 62.7, 110.0, 116.5, 123.3, 127.1,
127.7, 130.2, 159.2, 169.0. HRMS-EIþ: m/z Calcd for C12H13NO3:
219.0895; found: 219.0893.
4.2.18. Cyano(thiophen-2-yl)methyl acetate (entry 18)
1H NMR (CDCl3, 200 MHz): 2.12 (s, 3H), 6.60 (s, 1H), 7.01 (t,
J¼9 Hz, 1H), 7.35 (d, J¼6 Hz, 1H), 7.42 (d, J¼8 Hz, 1H). 13C NMR
(CDCl3, 400 MHz): 20.3, 58.1, 115.6, 127.2, 129.0, 129.6, 133.4,
168.8. HRMS-EIþ: m/z Calcd for C8H7NO2S: 181.0197; found:
191.0198.
4.2.7. (4-tert-Butylphenyl)(cyano)methyl acetate (entry 7)
1H NMR (CDCl3, 200 MHz): 1.33 (s, 9H), 2.15 (s, 3H), 6.39 (s, 1H),
6.94 (d, J¼8 Hz, 2H), 7.42 (d, J¼8 Hz, 2H). 13C NMR (CDCl3,
400 MHz): 20.5, 31.1, 34.8, 62.7, 116.2, 126.7, 127.7, 128.7, 153.2,
169.0. HRMS-EIþ: m/z Calcd for C14H17NO: 231.1259; found:
231.1257.
4.2.19. Cyano(pyridin-2-yl)methyl acetate (entry 19)
1H NMR (CDCl3, 200 MHz): 2.21 (s, 3H), 6.44 (s, 1H), 7.34 (t,
J¼13.6 Hz, 1H), 7.50 (d, J¼8.8 Hz, 1H), 7.78 (t, J¼8.6 Hz, 1H), 8.62 (d,