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A. Inoue et al.
LETTER
8597. g) Mastukawa, M.; Inanaga, J.; Yamaguchi, M.
Tetrahedron Lett. 1987, 28, 5877. h) Kunishima, M.; Tanaka,
S.; Kono, K.; Hioki, K.; Tani, S. Tetrahedron Lett. 1995, 36,
3707.
(5) Some examples for the syntheses of 2-aryltetrahydrofurans
have been reported: a) Tomooka, K.; Matsuzawa, K.; Suzuki,
K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6339.
b) Homma, K.; Mukaiyama, T. Chem. Lett. 1989, 259.
c) Brückner, C.; Lorey, H.; Reisig, H.-U. Angew. Chem. Int.
Ed. Engl. 1986, 25, 556; Angew. Chem. 1986, 98, 559.
(6) Muceniece, D. Ethylmagnesium Bromide in Encyclopedia of
Reagents for Organic Synthesis; Paquette, L. Ed.; Wiley:
Chichester, 1995; p 2486.
(7) The use of i-PrI instead of EtI provided 1a in decreased yield
(28%).
(8) Nishiyama, H.; Isaka, K.; Itoh, K.; Ohno, K.; Nagase, H.;
Matsumoto, K.; Yoshiwara, H. J. Org. Chem. 1992, 57, 407.
(9) Martin, G. J.; Mechin, B.; Leroux, Y.; Paulmier, C.; Meunier,
J. C. J. Organomet. Chem. 1974, 67, 327.
(13) Ashby et al. discussed the possibility of formation of 2-
iodotetrahydrofuran in the reaction of iodoalkane with
LiAlH4. Ashby, E. C.; Welder, C. O. J. Org. Chem. 1997, 62,
3542.
(14) Representative experimental procedure: To a solution of 4-
methoxyphenylmagnesium bromide (0.94 mL, 1.06 M THF
solution, 1.0 mmol) in THF (3 mL), neopentyl iodide (0.79 g,
4.0 mmol) and EtMgBr (2.0 mL, 1.01 M THF solution, 2.0
mmol) were added at 25° C under argon atmosphere. After 20
min, a white precipitate was formed. The mixture was stirred
for 5 h. Then, saturated aqueous NH4Cl (20 mL) was added to
the reaction mixture carefully and the whole was extracted
with hexane (10 mL X 3). Concentration and purification by
silica-gel column chromatography afforded 4-(2-
(10) a) Cadwick, D. J.; Willbe, C. J. Chem. Soc. Perkin. Trans. 1
1977, 887. b) Jones, E.; Moodie, I. M. Org. Synth. 1970, 50,
104.
(11) The use of other solvents in place of THF gave quite
unsatisfactory results. Using 2-methyltetrahydrofuran as a
solvent, 2-methyl-2-thienyltetrahydrofuran and 2-methyl-5-
thienyltetrahydrofuran were obtained in 12% and 23% yields,
respectively. The reaction in tetrahydropyran provided 2-
thienyltetrahydropyran in only 18% yield under the same
reaction conditions.
(12) a) Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486.
b) Xiang, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 11986.
c) Xiang, J.; Jiang, W.; Gong, J.; Fuchs, P. L. J. Am. Chem.
Soc. 1997, 119, 4123. d) Xiang, J.; Jiang, W.; Fuchs, P. L.
Tetrahedron Lett. 1997, 38, 6635. e) Xiang, J.; Evarts, J.;
Rivkin, A.; Curran, D. P.; Fuchs, P. L. Tetrahedron Lett. 1998,
39, 4163. f) Xiang, J.; Fuchs, P. L. Tetrahedron Lett. 1998, 39,
tetrahydrofuryl)-anisole (2a, 135 mg, 0.76 mmol) in 76%
yield: IR (neat) 2932, 2862, 1613, 1587, 1509, 1460, 1364,
1302, 1243, 1174, 1058, 1038, 919, 828 cm–1; 1H NMR
(CDCl3) d 1.71-1.85 (m, 1 H), 1.89-2.09 (m, 2 H), 2.20-2.32
(m, 1 H), 3.78 (s, 3 H), 3.90 (ddd, J = 6.6, 8.0, 8.0 Hz, 1 H),
4.07 (ddd, J = 6.9, 8.0, 8.0 Hz, 1 H), 4.82 (dd, J = 7.2, 6.9 Hz,
1 H), 6.86 (d, J = 8.6 Hz, 2 H), 7.26 (d, J = 8.6 Hz, 2 H); 13
NMR (CDCl3) d 25.67, 34.13, 54.80, 68.08, 80.13, 113.42,
C
126.73, 135.15, 158.68. Found: C, 74.29; H, 8.06. Calcd for
C11H14O2: C, 74.13; H, 7.92.
Article Identifier:
1437-2096,E;1999,0,10,1582,1584,ftx,en;Y14099ST.pdf
Synlett 1999, No. 10, 1582–1584 ISSN 0936-5214 © Thieme Stuttgart · New York