SELECTIVE FORMATION OF PRODUCTS OF INTERRUPTED FEIST-BENARY REACTION
801
3
2,6
(
1Н, ОН, J 6.8 Hz), 7.20 d (2H, H , J 7.8 Hz), 7.31
Crystallographic Data Centre, CCDC 1575255.
Melting points were measured on Boёtius apparatus.
аrom
3
,5
3,5
d (2H, H , J 7.8 Hz), 7.58 t [2H, H (PhSO ), J
аrom
2
4
8
.8 Hz], 7.66 t [1H, H (PhSO ), J 7.8 Hz], 7.83 d [2H,
2
2,6
REFERENCES
H (PhSO ), J 8.8 Hz]. Mass spectrum, m/z: 365 [M + 1,
2
3
5
+
37
+
Сl] , 367 [M + 1, Сl] . Found, %: С 59.34; H 4.74.
C H ClO S. Calculated, %: C 59.26; H 4.70.
1
. Matiychuk, V.S., Martyak, R.L., Obushak, N.D.,
Ostapiuk, Yu.V., and Pidlypnyi, N.I., Chem. Heterocycl.
Compd., 2004, vol. 40, p. 1218. doi 10.1023/
B:COHC.0000048299.17625.7f
1
8
17
4
5
-Methyl-2-(4-chlorobenzyl)-4-(4-chlorophenyl-
sulfonyl)-2,3-dihydrofuran-3-ol (3c). Yield 4.06 g
68%), mp 166–167°С. H NMR spectrum, δ, ppm:
.14 s (3Н, СН ), 2.80–2.84 m (2Н, CH ), 4.51 t.d
1
(
2
(
2
2. Pokhodylo, N.T., Matiychuk, V.S., and Obushak, M.D.,
Synthesis, 2009, p. 2321.
3
2
2
3
3
3
1Н, Н , J 6.5, 2.1 Hz), 4.69 d.d (1Н, Н , J 6.8,
3. Albrecht, L., Ransborg, L.K., Gschwend, B., and
Jorgensen, K.A., J. Am. Chem. Soc., 2010, vol. 132,
p. 17886.
furan
furan
3
2,6
аrom
.1 Hz), 5.71 d (1Н, ОН, J 7.1 Hz), 7.22 d (2H, H
J 7.8 Hz), 7.31 d (2H, H , J 7.8 Hz), 7.65 d [2H,
,
3
,5
аrom
3
,5
2,6
4
5
6
7
. Calter, M.A. and Korotkov, A., Org. Lett., 2011, vol. 13,
p. 6328.
. Calter, M.A. and Korotkov, A., Org. Lett., 2015, vol. 17,
p. 1385.
H (ArSO ), J 8.8 Hz], 7.83 d [2H, H (ArSO ), J
2
2
3
5
35
+
8
4
.8 Hz]. Mass spectrum, m/z: 399 [M + 1, Сl + Сl] ,
01 [M + 1, Сl + Сl] , 403 [М + 1, Сl + Сl] .
Found, %: С 54.05; H 3.92. C H Cl O S. Calculated,
: C 54.14; H 4.04.
3
5
37
+
37
37
+
1
8
16
2
4
. Sinha, D., Biswas, A., and Singh, V.K., Org. Lett.,
%
2
015, vol. 17, p. 3302.
1
Н NMR spectra were registered on a spectrometer
Varian Unity +400 at operating frequency 400 МHz in
. Ranu, B.C., Adak, L., and Banerjee, S., Tetrahedron
Lett., 2008, vol. 49, p. 4613.
DMSO-d , internal reference TMS. Mass spectra were
6
8. Calter, M.A., Phillips, R.M., and Flaschenriem, C.,
taken on a GC-MS instrument Agilent 1100 LC/MSD,
chemical ionization mode at atmospheric pressure.
Elemental analysis was carried out on an analyzer
Carlo Erba 1106. XRD experiment was performed of a
four-circle diffractometer Oxford Diffraction
Xcalibur3 equipped with a CCD-detector. The
structure was solved by the direct method after
analytical correction for extinction. The positions of
hydrogen atoms were calculated and refined using
restrictions SHELXL. Crystallographic data on
compound 3a were deposited to Cambridge
J. Am. Chem. Soc., 2005, vol. 127, p. 14566.
9
. Calter, M.A. and Zhu, C., Org. Lett., 2002, vol. 4, p. 205.
0. Calter, M.A., Zhu, C., and Lachicotte, R.J., Org. Lett.,
002, vol. 4, p. 209.
1
1
1
1
2
1. Moss, T.A. and Nowak, T., Tetrahedron Lett., 2012,
vol. 53, p. 3056.
2. Obushak, N.D., Matiichuk, V.S., and Ganushchak, N.I.,
Zh. Org. Khim., 1997, vol. 33, p. 1081.
3. Obushak, N.D., Matiichuk, V.S., Vasylyshin, R.Ya., and
Ostapyuk, Yu.V., Russ. J. Org. Chem., 2004, vol. 40,
p. 383. doi 10.1023/B:RUJO.0000034976.75646.85
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 5 2018