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4.3.1. 4-Phenyldihydrofuran-2(3H)-one (1b).3d Following general
CDCl3): d 7.56e7.30 (m, 2H), 7.30e7.08 (m, 2H), 4.77e4.54 (m, 1H),
procedure, a white solid was obtained. 1H NMR (300 MHz,
4.35e4.13 (m, 1H), 3.77 (dd, J¼15.3, 7.3 Hz, 1H), 3.01e2.81 (m, 1H),
CDCl3):
d 7.66e7.05 (m, 5H), 4.68e4.61 (m, 1H), 4.24 (t,
2.64 (ddd, J¼17.5, 8.8, 4.6 Hz, 1H) ppm. 13C NMR (75 MHz, CDCl3):
J¼8.5 Hz, 1H), 3.77 (p, J¼8.4 Hz, 1H), 2.90 (dd, J¼17.5, 8.7 Hz,
d 175.92, 141.85, 130.87, 130.75, 129.98, 125.34, 123.12, 73.60, 40.68,
1H), 2.65 (dd, J¼17.5, 9.2 Hz, 1H) ppm. 13C NMR (75 MHz,
35.50 ppm. HRMS calcd for C10H9BrO2 (MþH): 239.9786, found:
CDCl3):
d
176.48, 139.48, 129.17, 127.74, 126.76, 74.08, 41.12,
239.9789.
35.73 ppm. HRMS calcd for C10H10O2 (MþH): 162.0681, found:
162.0677.
4.3.9. 4-(5-Oxotetrahydrofuran-3-yl)phenyl acetate (9b). Following
general procedure, a colorless oil was obtained. 1H NMR (400 MHz,
4.3.2. 4-p-Tolyldihydrofuran-2(3H)-one (2b).3d Following general
CDCl3): d 7.58e6.73 (m, 4H), 4.87e4.51 (m, 1H), 4.43e4.09 (m, 1H),
procedure, a colorless oil was obtained. 1H NMR (400 MHz, CDCl3):
4.08e3.47 (m, 1H), 2.92 (dd, J¼16.2, 7.4 Hz, 1H), 2.65 (dd, J¼15.6,
d
7.17 (d, J¼8.0 Hz, 2H), 7.12 (d, J¼8.1 Hz, 2H), 4.63 (dd, J¼8.7, 8.1 Hz,
8.3 Hz, 1H), 2.30 (dt, J¼6.4, 3.7 Hz, 3H) ppm. 13C NMR (101 MHz,
1H), 4.28e4.11 (m, 1H), 3.74 (p, J¼8.4 Hz, 1H), 2.89 (dd, J¼17.5,
8.7 Hz, 1H), 2.64 (dd, J¼17.5, 9.2 Hz, 1H), 2.32 (d, J¼13.9 Hz, 3H)
CDCl3): d 176.52, 169.73, 150.29, 137.26, 128.06, 122.56, 74.18, 40.83,
35.98, 21.33 ppm. HRMS calcd for C12H12O4 (MþH): 220.0736,
ppm. 13C NMR (101 MHz, CDCl3):
d
175.48, 136.32, 135.25, 128.65,
found: 220.0740.
125.48, 73.07, 39.65, 34.65, 19.90 ppm. HRMS calcd for C11H12O2
(MþH): 176.0837, found: 176.0839.
4.3.10. 4-(4-tert-Butylphenyl)dihydrofuran-2(3H)-one (10b). Follow-
ing general procedure, a white solid was obtained. 1H NMR
4.3.3. 4-(4-Methoxyphenyl)dihydrofuran-2(3H)-one (3b).5b Follow-
(300 MHz, CDCl3): d 7.49e7.30 (m, 2H), 7.24e7.06 (m, 2H), 4.65 (dd,
ing general procedure, a colorless oil was obtained. 1H NMR
J¼8.9, 8.0 Hz, 1H), 4.26 (dd, J¼8.9, 8.3 Hz, 1H), 3.93e3.60 (m, 1H),
(300 MHz, CDCl3): d 7.23e6.99 (m, 2H), 7.02e6.75 (m, 2H), 4.64 (dd,
2.91 (dd, J¼17.5, 8.6 Hz, 1H), 2.67 (dd, J¼17.5, 9.4 Hz,1H),1.32 (s, 9H)
J¼8.9, 7.9 Hz, 1H), 4.22 (dd, J¼8.9, 8.2 Hz, 1H), 3.82 (d, J¼7.7 Hz, 3H),
ppm. 13C NMR (75 MHz, CDCl3):
d 176.61, 150.74, 136.32, 126.48,
3.79e3.60 (m, 1H), 2.90 (dd, J¼17.4, 8.6 Hz, 1H), 2.63 (dd, J¼17.4,
126.03, 74.15, 40.72, 35.77, 34.54, 31.31 ppm. HRMS calcd for
C14H18O2 (MþH): 218.1307, found: 218.1301.
9.3 Hz, 1H) ppm. 13C NMR (75 MHz, CDCl3):
d
176.56, 159.05, 131.30,
127.77, 114.49, 74.27, 55.34, 40.45, 35.88 ppm. HRMS calcd for
C11H12O3 (MþH): 192.0786, found: 192.0788.
4.3.11. 4-(Naphthalen-2-yl)dihydrofuran-2(3H)-one (11b).3d Follow-
ing general procedure, a white solid was obtained. 1H NMR
4.3.4. 4-(4-Fluorophenyl)dihydrofuran-2(3H)-one (4b).3d Following
(300 MHz, CDCl3):
d
8.01e7.73 (m, 3H), 7.67 (d, J¼0.9 Hz, 1H),
general procedure, a white solid was obtained. 1H NMR (400 MHz,
7.56e7.45 (m, 2H), 7.33 (dd, J¼8.5, 1.9 Hz, 1H), 4.73 (dd, J¼9.1, 7.9 Hz,
1H), 4.37 (dd, J¼9.1, 7.8 Hz, 1H), 3.94 (p, J¼8.3 Hz, 1H), 3.00 (dd,
J¼17.5, 8.7 Hz, 1H), 2.78 (dd, J¼17.5, 8.9 Hz, 1H) ppm. 13C NMR
CDCl3):
d
7.27e7.16 (m, 2H), 7.15e6.95 (m, 2H), 4.66 (dd, J¼9.0,
7.9 Hz, 1H), 4.24 (dd, J¼9.0, 7.8 Hz, 1H), 3.78 (p, J¼8.3 Hz, 1H), 2.93
(dd, J¼17.5, 8.7 Hz, 1H), 2.63 (dd, J¼17.5, 8.9 Hz, 1H) ppm. 13C NMR
(75 MHz, CDCl3):
d 176.15, 138.83, 133.51, 129.20, 128.28, 126.73,
(101 MHz, CDCl3):
d
176.44, 163.70, 161.24, 135.56, 135.53, 128.65,
124.39, 72.87, 40.15, 34.73 ppm. HRMS calcd for C14H12O2 (MþH):
128.57, 116.49, 116.27, 74.31, 40.76, 36.13 ppm. HRMS calcd for
212.0837, found: 212.0837.
C10H9FO2 (MþH): 180.0587, found: 180.0583.
4.3.12. 4-Methyl-4-phenyldihydrofuran-2(3H)-one (12b).14 Follow-
4.3.5. 4-(4-Chlorophenyl)dihydrofuran-2(3H)-one (5b).3d Following
ing general procedure, a colorless oil was obtained. 1H NMR
general procedure, a white solid was obtained. 1H NMR (400 MHz,
(300 MHz, CDCl3): d 7.42e7.15 (m, 5H), 4.41 (s, 2H), 2.91 (d,
CDCl3):
d
7.41e7.26 (m, 2H), 7.18 (d, J¼8.4 Hz, 2H), 4.65 (dd, J¼8.9,
J¼16.8 Hz, 1H), 2.67 (d, J¼16.8 Hz, 1H), 1.52 (s, 3H) ppm. 13C NMR
8.0 Hz, 1H), 4.23 (dd, J¼9.0, 7.8 Hz, 1H), 3.78 (p, J¼8.3 Hz, 1H), 2.92
(75 MHz, CDCl3): d 176.24, 144.30, 129.02, 127.24, 125.21, 78.40,
(dd, J¼17.5, 8.7 Hz, 1H), 2.62 (dd, J¼17.5, 8.9 Hz, 1H) ppm. 13C NMR
44.15, 41.99, 28.04 ppm. HRMS calcd for C11H12O2 (MþH):
(101 MHz, CDCl3):
d
176.07, 138.07, 133.47, 129.26, 128.14, 73.76,
176.0837, found: 176.0841.
40.50, 35.61 ppm. HRMS calcd for C10H9ClO2 (MþH): 196.0291,
found: 196.0297.
4.3.13. 4,4-Diphenyldihydrofuran-2(3H)-one
general procedure, a white solid was obtained. 1H NMR (300 MHz,
CDCl3):
7.57e6.91 (m, 10H), 4.83 (s, 2H), 3.19 (s, 2H) ppm. 13C NMR
(75 MHz, CDCl3): 175.54, 143.83, 128.99, 127.40, 126.48, 77.11,
(13b).15 Following
4.3.6. 4-(4-Bromophenyl)dihydrofuran-2(3H)-one (6b).3d Following
d
general procedure, a white solid was obtained. 1H NMR (400 MHz,
d
CDCl3):
d
7.66e7.33 (m, 2H), 7.26e6.97 (m, 2H), 4.66 (dd, J¼9.0,
52.49, 41.99 ppm. HRMS calcd for C16H14O2 (MþH): 238.0994,
7.9 Hz, 1H), 4.23 (dd, J¼9.1, 7.7 Hz, 1H), 3.76 (p, J¼8.3 Hz, 1H), 2.93
found: 238.0990.
(dd, J¼17.5, 8.7 Hz, 1H), 2.63 (dd, J¼17.5, 8.8 Hz, 1H) ppm. 13C NMR
(101 MHz, CDCl3):
d
176.27, 138.86, 132.61, 128.73, 121.94, 74.01,
4.3.14. 4-Benzyldihydrofuran-2(3H)-one (1d).5d Following general
40.91, 35.90 ppm. HRMS calcd for C10H9BrO2 (MþH): 239.9786,
procedure, a colorless oil was obtained. 1H NMR (300 MHz, CDCl3):
found: 239.9784.
d
7.58e6.85 (m, 5H), 4.31 (dd, J¼9.1, 6.8 Hz, 1H), 4.02 (dd, J¼9.1,
6.0 Hz, 1H), 2.91e2.78 (m, 1H), 2.75 (dd, J¼8.2, 5.4 Hz, 2H), 2.58 (dd,
4.3.7. 4-(2-Bromophenyl)dihydrofuran-2(3H)-one (7b).3d Following
J¼17.5, 7.8 Hz, 1H), 2.27 (dd, J¼17.5, 6.9 Hz, 1H) ppm. 13C NMR
general procedure, a colorless oil was obtained. 1H NMR (300 MHz,
(75 MHz, CDCl3): d 176.94, 138.31, 128.81, 128.70, 126.81, 72.69,
CDCl3):
d
7.61 (dd, J¼8.0, 0.6 Hz, 1H), 7.35 (t, J¼7.5 Hz, 1H), 7.29 (dd,
38.90, 37.17, 34.24 ppm. HRMS calcd for C11H12O2 (MþH): 176.0837,
J¼7.8, 1.7 Hz, 1H), 7.17 (t, J¼7.5 Hz, 1H), 4.71 (t, J¼8.0 Hz, 1H), 4.31
(dd, J¼8.1, 7.1 Hz, 1H), 4.22 (dd, J¼14.0, 7.0 Hz, 1H), 2.98 (dd, J¼17.6,
8.6 Hz, 1H), 2.67 (dd, J¼17.5, 6.6 Hz, 1H) ppm. 13C NMR (75 MHz,
found: 176.0831.
4.3.15. 4-(4-Methoxybenzyl)dihydrofuran-2(3H)-one (2d).5d Follow-
CDCl3):
d
176.15,138.83,133.51,129.20,128.28,126.73,124.39, 72.87,
ing general procedure, a colorless oil was obtained. 1H NMR
40.15, 34.73 ppm. HRMS calcd for C10H9BrO2 (MþH): 239.9786,
(300 MHz, CDCl3): d 7.20e6.94 (m, 2H), 7.00e6.65 (m, 2H), 4.32
found: 239.9787.
(dd, J¼9.2, 6.8 Hz, 1H), 4.10e3.95 (m, 1H), 3.79 (s, 3H), 2.90e2.75
(m, 1H), 2.76e2.64 (m, 2H), 2.59 (dd, J¼17.5, 7.9 Hz, 1H), 2.27 (dd,
4.3.8. 4-(3-Bromophenyl)dihydrofuran-2(3H)-one (8b). Following
J¼17.5, 6.9 Hz, 1H) ppm. 13C NMR (75 MHz, CDCl3):
d 177.01,
general procedure, a colorless oil was obtained. 1H NMR (300 MHz,
158.42, 130.30, 129.65, 114.16, 72.67, 55.27, 38.00, 37.31,