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Typical Experiment
Procedure: To a solution of 5 (20
mg, 0.063 mmol) in CH2Cl2 (0.6 mL) was added
mercury triflate (0.01 M solution in MeCN, 6.3 µL, 0.063 µmol)
at r.t., and the mixture was stirred for 24 h. After addition of
sat. NaHCO3 solution, the dried and concentrated residue
was subjected to a column chromatography on silica gel using hexane-EtOAc
(12:1) as eluent to give 6 (18.4 mg, 98%)
as a colorless powder; mp 111 ˚C. IR (neat): 3066, 1598,
1354, 1165 cm-¹. ¹H
NMR (300 MHz, CDCl3): δ = 7.65 (d, J = 8.1 Hz, 1 H), 7.57 (d, J = 8.1 Hz, 2 H), 7.21 (m, 1
H), 7.17 (d,
J = 8.1
Hz, 1 H), 7.01-7.07 (m, 2 H), 6.99 (dd, J = 0.9,
7.5 Hz, 1 H), 5.91 (ddd, J = 6.3,
10.2, 16.8 Hz, 1 H), 5.39 (dt,
J = 1.2,
16.8 Hz, 1 H), 5.15 (dt, J = 1.5,
10.2 Hz, 1 H), 4.74 (m, 1 H), 2.95 (dd, J = 9.9,
15.9 Hz, 1 H), 2.64 (dd, J = 3.3, 15.9
Hz, 1 H), 2.36 (s, 3 H). ¹³C NMR (75
MHz, CDCl3):
δ = 143.8, 141.4,
137.6, 135.3, 131.2, 129.5, 127.7, 127.1, 125.1, 124.5, 116.8, 115.7,
63.8, 34.9, 21.5. HRMS (EI):
m/z [M]+ calcd
for C17H19NO3S+:
299.0980; found: 299.0999.
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