3786
A. Gupta, S. Ray
PAPER
3-(Ethoxyphenyl)-7-methoxy-3,4-dehydrochroman (18)
To a solution of 15 (1.49 g, 5.0 mmol) in MeOH (50 mL) was added
NaBH4 (76 mg) in portions at 0 °C. After 30 min at 0 °C, the mixture
was stirred at r.t. for 5 h. On completion of the reaction, the solvent
was evaporated and aq sat. NH4Cl (50 mL) was added to the mixture
followed by its extraction with EtOAc (5 × 50 mL). The combined
organic layers were dried (Na2SO4) and concentrated to give an oily
residue. The crude residue was dissolved in EtOH (25 mL) and few
drops of concd HCl was added to this solution. The mixture was
then refluxed for 1.3 h. The solvent was evaporated and the residue
was dissolved in EtOAc (50 mL) and washed with H2O (100 mL).
The organic layer was dried (Na2SO4) and concentrated to give an
oily residue. The crude material was purified on silica gel column
using EtOAc–hexane as eluent; yield: 1.13 g (80%); mp 153–
155 °C.
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IR (KBr): 1609, 1511, 1388, 1351, 1279, 1159, 1034, 830 cm–1.
1H NMR (CDCl3): d = 1.32 (t, J = 6.90 Hz, 3 H, CH3), 3.68 (s, 3 H,
OCH3), 3.93 (q, J = 6.60 Hz, 2 H, CH2), 6.39–6.35 (m, 2 H, CH2),
6.56 (s, 1 H, CH), 6.79 (d, J = 8.70 Hz, 2 H, ArH), 6.88 (d, J = 8.10
Hz, 1 H, ArH), 7.23 (d, J = 8.70 Hz, 2 H, ArH).
FAB-MS: m/z = 281 (M – 1), 282.
Anal. Calcd for C18H18O3: C, 76.57; H, 6.43. Found: C, 76.31; H,
6.61.
4,4¢-Dihydroxy-3-phenyl-3,4-dehydrochroman (4)
Compound 4 was synthesized from compound 18 (0.5 g, 18 mmol)
following the same experimental procedure used for the synthesis of
compound 3 from 16; yield: 0.32 g (75%); mp 165–166 °C.
IR (KBr): 1607, 1510, 1388, 1351, 1279, 1159, 1034, 825 cm–1.
1H NMR (CDCl3): d = 5.10 (d, J = 1.60 Hz, 2 H, CH2), 6.33 (d,
J = 2.30 Hz, 1 H, ArH), 6.41 (dd, J = 2.20, 8.10 Hz, 1 H, ArH), 6.60
(s, 1 H, CH), 6.87 (d, J = 8.45 Hz, 2 H, ArH), 6.94 (d, J = 8.00 Hz,
1 H, ArH), 7.36 (d, J = 8.00 Hz, 2 H, ArH).
FAB-MS: m/z = 240.
Anal. Calcd for C15H12O3: C, 74.99; H, 5.03. Found: C, 75.05; H,
5.32.
Acknowledgment
Atul Gupta is thankful to the Council of Scientific and Industrial
Research, Government of India, for a senior research fellowship
(SRF). Authors are thankful to Sophisticated Analytical and Instru-
ment Facilities (SAIF), CDRI, Lucknow for providing spectrosco-
pic analysis.
References
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Chem. 1978, 31, 455. (b) Heaton, A.; Jeoffreys, G. PCT Int.
Appl. WO 2005103025, 2005; Chem. Abstr. 2005, 143,
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(1) Present and corresponding address: Département de Chimie-
Biologie, Université de Quebec à Trois-Rivières, C.P. 500,
Trois-Rivières, QC, G9A 5H7, Canada.
Synthesis 2008, No. 23, 3783–3786 © Thieme Stuttgart · New York