P.E. da Silva Júnior, N. M. de Araujo, and F. da Silva Emery
Vol 000
REFERENCES AND NOTES
chromatography (hexane/ethyl acetate, 9:1) to afford a orange
crystal, 2, 89%. mp: 156°C. 1H-NMR (300 MHz, CDCl3):
δ 1.49 (s, 6H), 5.64 (d, J = 12 Hz, 1H), 6.57 (d, J = 9 Hz, 1H),
7.63 (m, 2H), and 8.01 (m, 2H). 13C-RMN (75 MHz, CDCl3):
δ 181.9, 179.8, 152.4, 133.9, 133.2, 131.6, 131.5, 130.8, 126.2,
117.9, 117.8, 115.5, 80.5, and 28.4. IR (cmÀ1): 2918, 2357,
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[5] Hlubucek, J.; Ritchie, E.; Taylor, W. C., Tetrahedron Lett 1969,
17, 1369.
1651, 1271, 966, and 717. HRMS: (M+1
C15H13O+3: 241.0859, obtained: 241.0856
) calculated to
[6] Meepagala, K. M.; Schrader, K. K.; Burandt, C. L.; Wedge, D.
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3,3-dimethyl-2-methylene-2,3-dihydronaphtho[2,3-b]furan-
4,9-dione (4). To a solution of 1 (0,14 mmol, 25 mg) in CH3CN
(10 mL) under stirring at 0°C, was added DBU (0.5mmol,
0.07 mL), CuI (14 μmol, 2.6 mg) and 3,3-chloro-3-methylbut-1-
yne (0.5mmol, 0.055mL). The reaction was heated until room
temperature and then maintained under reflux for 24h. The
solvent was removed under reduced pressure and the residue was
poured into cold water, the aqueous phase was washed with ethyl
acetate (3× 10mL). The organic layer was washed with brine
solution and dried by Na2SO4. The solvent was removed under
reduced pressure and purified by flash column chromatography
(hexane/ethyl acetate, 9:1) to afford a yellow crystal, 83%. mp
1
137°C. H-RMN (300 MHz, CDCl3): δ 1.52 (s, 6H), 4.4 (d, J = 3
Hz, 1H), 4.86 (d, J = 6 Hz, 1H), 7.66 (m, 2H), and 8.02 (m, 2H).
13C-RMN (75 MHz, CDCl3): δ 181.24, 177.08, 169.9, 156.0,
134.33, 133.19, 133.14, 131.5, 131.2, 126.34, 126.2, 87.14,
45.43, and 28.13. IR (cmÀ1): 2918, 2357, 1651, 1271, 966, and
717. HRMS: (M+1) calculated to C15H13O+3: 241.0859, obtained:
241.0855
Acknowledgments. We thank Prof. Dr. Roberto Santana da
Silva and his equip for IR spectra. We would to also thank
CAPES, FAPESP, and INCT_if for scholarship and grants.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet