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K. L. Cosgrove, R. P. McGeary
LETTER
(10) Boezio, A. A.; Solberghe, G.; Lauzon, C.; Charette, A. B.
J. Org. Chem. 2003, 68, 3241.
(11) Bergman, J.; Sand, P. Org. Synth. 1987, 65, 146.
(12) DeWolfe, R. H. In Organic Chemistry, Vol. 14; Academic
Press: New York, 1970, 299.
(13) Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom,
T. J.; Li, T.-T.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem.
Soc. 1970, 92, 741.
(27) Kuryla, W. C.; Leis, D. G. J. Org. Chem. 1964, 29, 2773.
(28) Ikejiri, M.; Miyashita, K.; Tsunemi, T.; Imanishi, T.
Tetrahedron Lett. 2004, 45, 1243.
(29) Bianco, A.; Romagnoli, P. Synth. Commun. 1998, 28, 3179.
(30) Compound 14: light yellow oil. 1H NMR (400 MHz,
CDCl3): d = 4.59 (s, 2 H), 4.09–4.23 (m, 4 H), 3.27 (s, 6 H),
3.23 (s, 6 H), 1.42 (s, 6 H), 1.26 (t, 6 H, J = 7.2 Hz). 13C NMR
(100 MHz, CDCl3): d = 169.8, 115.4, 60.9, 50.33, 50.31,
19.7, 14.1. HRMS (ESI, +ve): m/z [M + Na]+ calcd for
C16H30O10: 405.1737; found: 405.1732.
(14) Hill, R. K.; Soman, R.; Sawada, S. J. Org. Chem. 1972, 37,
3737.
(15) Merisor, E.; Conrad, J.; Malakar, C. C.; Beifuss, U. Synlett
2008, 903.
(16) Perron, F.; Gahman, T. C.; Albizati, K. F. Tetrahedron Lett.
1988, 29, 2023.
(17) Haudrechy, A.; Picoul, W.; Langlois, Y. Tetrahedron:
Asymmetry 1997, 8, 139.
(18) Beyerstedt, F.; McElvain, S. M. J. Am. Chem. Soc. 1936, 58,
529.
(19) McElvain, S. M.; Stevens, C. L. J. Am. Chem. Soc. 1946, 68,
1917.
(20) McElvain, S. M.; McKay, G. R. J. Am. Chem. Soc. 1955, 77,
5601.
(21) McElvain, S. M.; Morris, L. R. J. Am. Chem. Soc. 1952, 74,
2657.
(22) Barnes, H. M.; Kundiger, D.; McElvain, S. M. J. Am. Chem.
Soc. 1940, 62, 1281.
(23) McElvain, S. M.; Kundiger, D. J. Am. Chem. Soc. 1942, 64,
254.
(24) Ohshima, M.; Murakami, M.; Mukaiyama, T. Chem. Lett.
1984, 13, 1535.
(25) Capon, B.; Siddhanta, A. K. J. Org. Chem. 1984, 49, 255.
(26) Capon, B.; Siddhanta, A. K.; Zucco, C. J. Org. Chem. 1985,
50, 3580.
(31) Compound 16: yellow oil. 1H NMR (400 MHz, C6D6): d =
6.00 (ddd, 1 H, 3Jtrans = 17.4 Hz, 3Jcis = 10.6 Hz, 3J = 6.1 Hz),
5.32 (br dt, 1 H, 3Jtrans = 17.2 Hz, 2J = 1.5 Hz, 4J = 1.5 Hz),
5.06 (ddd, 1 H, 3Jcis = 10.6 Hz, 2J = 1.8 Hz, 4J = 1.4 Hz), 4.57
(qt, 1 H, 3J = 6.1 Hz, 4J = 1.3 Hz), 3.79 (dd, 1 H, 2J = 9.7 Hz,
3J = 6.1 Hz), 3.62 (dd, 1 H, 2J = 9.7 Hz, 3J = 5.9 Hz), 3.20 (s,
3 H), 3.19 (s, 3 H), 3.17 (s, 3 H), 3.16 (s, 3 H), 1.42 (s, 3 H),
1.34 (s, 3 H). 13C NMR (100 MHz, C6D6): d = 138.7, 128.9,
115.4, 114.8, 72.6, 66.0, 49.8, 49.7, 49.6, 49.5, 20.8, 19.4.
MS (ESI): m/z = 287 [M + Na]+. HRMS (ESI, +ve): m/z
[M + Na]+ calcd for C12H24O6: 287.1470; found: 287.1454.
(32) In a typical experiment, ketene dimethyl acetal (3 mmol per
hydroxyl group) was added cautiously to the anhyd alcohol
(1 mmol) and stirred rapidly at r.t. under argon for 30 min.
The reaction was followed by neutral alumina TLC. After
complete conversion into the mixed ortho ester, the excess
ketene dimethyl acetal was removed in vacuo resulting in
pure mixed ortho ester in quantitative yield. Toluene-d8 and
C6D6 were used for most NMR samples because trace
amounts of HCl in CDCl3 resulted in decomposition of the
mixed ortho ester.33
(33) All compounds synthesised were characterised by 1H, 13
NMR and/or HRMS and elemental analysis.
C
Synlett 2008, No. 16, 2425–2428 © Thieme Stuttgart · New York