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Representative
Experimental Procedure: A THF suspension (5 mL) of NaH (78
mg, 3.25 mmol) and 3b (556 mg, 1.43 mmol)
was stirred under nitrogen atmosphere at 0 °C
for 30 min. A THF solution (10 mL) of 2a (190
mg, 1.1 mmol) was added and the solution was stirred for 60 min
at 0 °C. The reaction mixture was refluxed for
24 h, cooled and subsequently stirred for 12 h at 20 °C.
To the mixture was added diethyl ether (30 mL), an aqueous solution
of HCl (5 mL, 1 M) and a saturated solution of NaCl. The aqueous layer
was separated and extracted with CH2Cl2 (3 × 10
mL). The combined organic layers were dried (MgSO4),
filtered and the solvent of the filtrate was removed in vacuo. The residue
was purified by column chromatography (silica gel, diethyl ether/petroleum
ether = 1:20) to give 4b (52%)
as a yellow solid. Spectroscopic data of 4b: 1H
NMR (CDCl3, 250 MHz): δ = 1.42
(t, 3
J = 7
Hz, 3 H, CH3), 4.45 (q, 3
J = 7 Hz,
2 H, OCH
2CH3),
6.91 (dd, 3
J
1 = 7
Hz, 3
J
2 = 8
Hz, 1 H, Ar), 7.08 (d, 3
J = 8
Hz, 1 H, Ar), 7.10 (d, 3
J = 8
Hz, 1 H, Ar), 7.53 (dd, 3
J
1 = 7
Hz, 3
J
2 = 8
Hz, 1 H, Ar), 7.59 (d, 3
J = 8
Hz, 1 H, Ar), 7.84 (d, 3
J = 8
Hz, 1 H, Ar), 8.30 (s, 1 H, Ar), 11.34 (s, 1 H, OH), 11.87 (s, 1
H, OH). 13C NMR (CDCl3,
50 MHz): δ = 14.15 (CH3),
62.07 (CH2), 112.47, 119.03, 129.00 (C, Ar, ortho and para to
OH), 117.74, 118.51, 118.70 (CH, Ar, ortho and para to OH), 132.36, 132.95, 136.18,
136.59 (CH, Ar, meta to OH), 163.00,
164.70, 169.61 (C, C-OH, CO2Et), 199.12 (C,
CO). IR (KBr): 3178 (w), 3059 (w), 2987 (w), 2933 (w), 1683 (s),
1629 (s), 1589 (s), 1467 (m), 1444 (m), 1397 (m), 1343 (s), 1293
(s), 1262 (s), 1242 (s), 1176 (m), 1084 (m) cm-1.
MS (70 eV): m/z (%) = 286
(100) [M+], 121(94). Anal.
Calcd for C16H14O5: C, 67.31; H,
4.93. Found: C, 66.88; H, 5.18. All compounds gave satisfactory
spectroscopic and analytical and/or high resolution mass
data.
