TATARINOVA et al.
660
reported in [21]: yield 88% (2a), 94% (2b), 91% (2c).
The physical constants and spectral parameters of 2a–
2c were in agreement with those given in [21]. Oximes
3a–3c were synthesized by stirring a mixture of
2 mmol of 2a–2c and 0.21 g (3 mmol) of hydroxyl-
amine hydrochloride in 4 mL of pyridine for 24 h at
room temperature. The mixture was poured into cold
water (20 mL), and the precipitate was filtered off,
washed with water, dried under reduced pressure, and
recrystallized from hexane.
IR spectrum, ν, cm–1: 3300, 3078, 3060, 2955, 2921,
2870, 1935, 1788, 1711, 1653, 1611, 1570, 1495,
1447, 1343, 1312, 1283, 1207, 1186, 1101, 1045, 993,
907, 817, 751, 708, 651, 590, 515. 1H NMR spectrum,
3
δ, ppm: 1.04 d (3H, 4-CH3, J = 6.8 Hz), 1.54 m (1H,
3-H), 1.73 s (3H, CH3C=N), 2.70 m (1H, 4-H), 2.78 m
(1H, 3-H), 3.80 s and 3.82 s (3H each, CH3O), 5.36 s
(1H, 5-H), 6.81–7.28 m (8H, Harom), 8.48 br.s (1H,
OH). 13C NMR spectrum, δC, ppm: 9.9 (4-CH3), 21.1
(CH3C=N), 25.4 (C4), 40.8 (C3), 55.1 and 55.2
(CH3O), 82.1 (C2), 105.5 (C5); 110.2, 111.2, 112.5,
113.1 (C2′, C2″, C6′, C6″); 116.7 and 117.4 (C4′, C4″),
129.2 and 129.3 (C5′, C5″), 137.1 (C1″), 144.7 (C1′),
148.0 (C6), 159.4 and 159.5 (C3′, C3″), 159.6 (C=N).
Found, %: C 71.76; H 6.78; N 3.98. C22H25NO4. Cal-
culated, %: C 71.91; H 6.86; N 3.81.
(E)-1-(4-Methyl-2,6-diphenyl-3,4-dihydro-2H-
pyran-2-yl)ethan-1-one oxime (3a). Yield 0.52 g
(85%), white powder, mp 112–114°C. IR spectrum, ν,
cm–1: 3226, 3060, 2957, 2919, 2870, 1955, 1888, 1811,
1716, 1653, 1603, 1493, 1449, 1343, 1309, 1283,
1217, 1176, 1101, 998, 906, 807, 761, 699, 652, 500.
3
1H NMR spectrum, δ, ppm: 1.05 d (3H, 4-CH3, J =
The IR spectra were recorded on a Bruker IFS25
spectrometer; samples were prepared as films from
6.8 Hz), 1.56 m (1H, 3-H), 1.75 s (3H, CH3C=N),
2.72 m (1H, 4-H), 2.80 m (1H, 3-H), 5.37 s (1H, 5-H),
7.39–7.28 m (6H, Harom), 7.58 d (2H, o′-H, J = 7.8 Hz),
7.70 d (2H, o-H, J = 7.7 Hz), 8.29 br.s (1H, OH).
13C NMR spectrum, δC, ppm: 10.0 (4-CH3), 21.2
(CH3C=N), 25.5 (C4), 40.9 (C3), 82.1 (C2), 105.1
(C5), 124.3 and 125.1 (Co, Co′), 127.5 and 127.9
(Cp, Cp′), 128.3 and 128.4 (Cm, Cm′), 135.6 (Ci′), 143.0
(Ci), 148.3 (C6), 159.7 (C=N). Found, %: C 78.15;
H 6.89; N 4.56. C20H21NO2. Calculated, %: C 78.26;
H 6.80; N 4.53.
1
chloroform solution. The H and 13C NMR spectra
were measured on a Bruker DPX-400 spectrometer at
400.1 and 100.6 MHz, respectively, using CDCl3 as
solvent and hexamethyldisiloxane as internal standard.
The elemental analyses were obtained with a Flash EA
1112 Series analyzer.
This study was performed under financial support
by the Russian Science Foundation (project no. 14-
13-00588).
(E)-1-[4-Methyl-2,6-bis(4-methylphenyl)-3,4-di-
hydro-2H-pyran-2-yl]ethan-1-one oxime (3b). Yield
0.53 g (79%), white powder, mp 71–73°C. IR spec-
trum, ν, cm–1: 3302, 3087, 3030, 2957, 2922, 2871,
2735, 1907, 1796, 1710, 1654, 1614, 1570, 1511,
1449, 1363, 1344, 1290, 1223, 1185, 1103, 1048, 995,
906, 815, 732, 648, 652, 581, 520. 1H NMR spectrum,
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3-H), 1.74 s (3H, CH3C=N), 2.32 s and 2.33 s (3H
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(4-CH3), 21.0 and 21.2 (CH3C6H4), 21.3 (CH3C=N),
25.4 (C4), 41.0 (C3), 82.0 (C2), 104.2 (C5), 124.2 and
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137 (Cp, Cp′), 137.7 (Ci′), 140.2 (Ci), 148.4 (C6), 159.8
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(E)-1-[2,6-Bis(3-methoxyphenyl)-4-methyl-3,4-
dihydro-2H-pyran-2-yl]ethan-1-one oxime (3c).
Yield 0.60 g (82%), off-white powder, mp 63–65°C.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 54 No. 4 2018