1608
S. NADEEM AND A. S. DEMIR
1
45 mg of the product was obtained as slight yellow viscous liquid corresponding to 70%
1
yield. EI-MS: m/z = 296.3. H NMR (400 MHz, CDCl3): δ = 7.52 (m, 2 H), 7.37 (m, 2H),
7
.3 (m, 1H), 4.0 (d, J = 16.0 Hz, 1H), 3.87 (d, J = 16.0 Hz, 1H), 3.69 (d, J = 8.0 Hz, 3H,
OCH3), 3.61 (d, J = 8.0 Hz, 3H, OCH3), 2.98 (t, J = 16.0 Hz, 1H), 2.70 (d, J = 16.0 Hz,
13
1
1
1
H), 1.70 (s, 3H, CH3), 1.35 (s, 3H, CH3). C NMR (100 MHz, CDCl3): δ = 135.9, 129.9,
28.2 (d, JPC = 3 Hz), 127.9 (d, JPC = 2.9 Hz), 127.8 (d, JPC = 4.4 Hz), 123.6 (d, JPC =
.5 Hz), 121.0 (d, JPC = 10.9 Hz), 64.6 (d, JPC = 10.9 Hz), 54.1 (d, JPC = 6.5 Hz), 53.9
(d, JPC = 7.3 Hz), 32.7, 18.7, 13.8.
Dimethyl (2-(4-chlorophenyl)-4,5-dimethyl-3,6-dihydro-2H-pyran-2-yl)
phosphonate (3b)
1
39 mg (70%) of 3b was obtained as slight yellow viscous liquid. EI-MS: m/z =
1
3
4
3
(
1
2
30.08. H NMR (400 MHz, CDCl3): δ = 7.37 (dd, J = 12.0 Hz, J = 4.0 Hz, 2H), 7.27
3
3
d, J = 8.0 Hz, 2H), 3.93 (d, J = 16.0 Hz, 1H), 3.74 (d, J = 16.0 Hz, 1H), 3.64 (dd, JPH =
3
0.6 Hz, 3H, OCH3), 3.60 (d, JPH = 10.3 Hz, 3H, OCH3), 2.89 (t, JPH = 16.1 Hz, 1H),
13
.55 (d, J = 16.0 Hz, 1H), 1.62 (s, 3H, CH3), 1.28 (s, 3H, CH3). C NMR (100 MHz,
CDCl3): δ = 134.7, 133.9 (d, JPC = 3.6 Hz), 131.3, 129.3 (d, JPC = 5.1 Hz), 128.4 (d, JPC =
2
(
.9 Hz), 123.7 (d, JPC = 1.5 Hz), 120.9 (d, JPC = 10.9 Hz), 64.6 (d, JPC = 10.9 Hz), 54.2
d, JPC = 6.6 Hz), 54.0 (d, JPC = 7.3 Hz), 32.7, 18.7, 13.7.
Dimethyl (2-(4-methoxyphenyl)-4,5-dimethyl-3,6-dihydro-2H-pyran-2-yl)
phosphonate (3c)
1
16 mg (58%) of 3c was obtained as slight yellow viscous liquid. EI-MS: m/z =
1
3
4
3
(
1
26.13. H NMR (400 MHz, CDCl3): δ = 7.35 (dd, J = 8.8 Hz, J = 2.3 Hz, 2H), 6.84
3
d, J = 9.0 Hz, 2H), 3.89 (d, J = 15.6 Hz, 1H), 3.74 (s, 3H, OCH3), 3.73 (d, J = 16.0 Hz,
3
3
H), 3.61 (d, JPH = 10.3 Hz, 3H, OCH3), 3.57 (d, JPH = 10.3 Hz, 3H, OCH3), 2.88
(
t, JPH = 15.0 Hz, 1H), 2.57 (d, J = 16.8 Hz, 1H), 1.63 (s, 3H, CH3), 1.29 (s, 3H, CH3).
1
3
C NMR (100 MHz, CDCl3): δ = 159.3, 149.6, 134.5, 129.5, 121.2 (d, JPC = 10.9 Hz),
1
5
23.7, 120.9 (d, JPC = 10.9 Hz), 113.7 (d, JPC = 2.9 Hz), 64.4 (d, JPC = 10.9 Hz), 55.2,
4.1 (d, JPC = 7.3 Hz), 53.8 (d, JPC = 7.3 Hz), 32.6, 18.6, 13.8.
Dimethyl (2-(4-fluorophenyl)-4,5-dimethyl-3,6-dihydro-2H-pyran-2-yl)
phosphonate (3d)
1
24 mg (61%) of 3d was obtained as slight yellow viscous liquid. EI-MS: m/z =
1
3
1
1
14.11; H NMR (400 MHz, CDCl3): δ = 7.4 (m, 2H), 6.98 (m, 2H), 3.92 (d, J = 15.6 Hz,
3
3
H), 3.73 (d, J = 16.0 Hz, 1H), 3.63 (d, JPH = 10.2 Hz, 3H, OCH3), 3.59 (d, JPH =
0.2 Hz, 3H, OCH3), 2.90 (t, JPH = 15.6 Hz, 1H), 2.57 (d, J = 16.0 Hz, 1H), 1.63 (s, 3H
13
CH3), 1.29 (s, 3H CH3). C NMR (100 MHz, CDCl3): δ = 163.7 (d, JPC = 3.7 Hz), 161.2
13
19
(
2
(
d, JPC = 3.7 Hz), 132.4 (d, JPC = 5.0 Hz), 129.7 (d, JCF = 4.4 Hz, C, F), 123.7 (d, JPC =
.2 Hz), 120.9 (d, JPC = 10.9 Hz), 113.7 (d, JFC = 2.9 Hz), 64.6 (d, JPC = 13.4 Hz), 54.1
d, JPC = 7.3 Hz), 53.9 (d, JPC = 7.3 Hz), 32.8, 18.6, 13.7.