S. Aida et al. / Tetrahedron Letters 53 (2012) 5578–5581
5581
nitrogen for 5 min. To the clear solution, 0.5 mL of acetone was added and the
tube was stoppered. The reaction mixture was subsequently irradiated in a
Rayonet chamber reactor (RMR-600 model equipped with 8 Â UVB lamps,
8 Â 4 W). After evaporation of the solvent and drying, the conversion was
determined by 1H NMR spectroscopy of the crude product (CDCl3, DMSO-d6
Acknowledgements
This research was financially supported by James Cook Univer-
sity (JCU-CRIG 2011), the Global Initiatives Program and partially a
Grant-in-Aid for Scientific Research (Ministry of Education, Cul-
ture, Sports, Science and Technology of the Japanese Government)
and the Student Exchange Support Program from the Japan Student
Service Organization (JASSO). The authors thank Associate Profes-
sor Bruce Bowden and Dr. Murray Davies (JCU) for technical
assistance.
[5 vol %]). The signal integration for the single methine proton in
3 was
typically compared to the signal integration for the 2 equiv olefinic protons of
1. Pure products were isolated after trituration with warm n-hexane in an
ultrasound bath. Selected physical and spectral data for 2,2-dimethyl-5-
oxotetrahydrofuran-3-carboxylic acid (terebic acid, 3): colorless solid, mp
174–176 °C (Lit.23: 174 °C). 1H NMR (500 MHz, CDCl3, acetone-d6 [5 vol %]): d
(ppm) = 1.31 (s, 3 H, CH3), 1.56 (s, 3 H, CH3), 2.62 (dd, J = 17.5 Hz, J = 8.5 Hz 1 H,
CH2), 2.99 (dd, J = 17.5 Hz, J = 9.5 Hz 1 H, CH2), 3.17 (dd, J = 8.5 Hz, J = 9.5 Hz 1
H, CH), 3.40 (br s, 1 H, OH). 13C NMR (125 MHz, CDCl3, acetone-d6 [5 vol %]): d
(ppm) = 23.3 (q, 1 C, CH3), 28.5 (q, 1 C, CH3), 32.0 (t, 1 C, CH2), 50.3 (d, 1 C, CH),
References and notes
84.6 (s,
1 C, Cq), 171.3 (s, 1 C, C@O), 174.6 (s, 1 C, C@O). IR (KBr): m
(cmÀ1) = 3105, 2989, 1736, 1293, 1197, 1166, 1119, 744, 659. MS (CI): m/
z = 159 [M+1]+, 141, 113, 99, 69. HR-MS (CI): Calcd. [M+H]+: 159.0652 C7H11O4.
Found [M+H]+: 159.0661.
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