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14 Typical experimental procedure: A
solution of 16 (70 mg, 0.26 mmol) in toluene
(10 mL) was heated in a sealed tube at 160 °C for 10 h.
After removal of the solvent, the crude residue was purified by
column chromatography on silica gel using a mixture of hexanes/EtOAc
(7:1) as eluent, giving 50 mg (71%) of 19 as
a pale yellow oil. 1H NMR (250 MHz, CD3Cl) δ:
8.16 (s, 1 H, ArH), 7.94-7.87
(m, 2 H, ArH), 7.72-7.64 (m,
1 H, ArH), 7.55-7.46 (m, 2 H,
ArH), 7.31 (td, J = 7.2
Hz, 1.6 Hz, 1 H, ArH), 7.13 (td, J = 8.5 Hz, 1.3 Hz, 1 H, ArH), 7.05 (dd, J = 7.9
Hz, 1.3 Hz, 1 H, ArH), 5.15 (s, 2 H,
CH
2), 2.71 (s, 3 H, CH
3). 13C
NMR + DEPT (62.83 MHz, CD3Cl) δ: 206.1
(CO), 155.0 (C),
136.1 (C), 133.2 (C),
129.9 (CH), 128.8 (CH),
128.2 (C), 128.0 (C),
127.0 (CH), 126.6 (CH),
126.2 (C), 124.3 (CH),
123.8 (CH), 122.5 (CH),
122.4 (C), 122.1 (CH),
117.6 (CH), 66.1 (CH2),
33.1 (CH3). EM m/z (%): 274 (M+,
100), 273 (45), 231 (61), 202 (53). HRMS C19H14O2:
calcd 274.09938, found 274.09940.