Z. Li, M. K. Gupta, T. S. Snowden
FULL PAPER
ent to obtain 68 mg (0.42 mmol, 84% yield from the reaction con-
ducted at 40 °C) of the indicated compound as a colorless oil. IR
W. Reeve, J. C. Hoffsommer, P. F. Auotto, Can. J. Chem. 1968,
46, 2233–2238; f) W. Reeve, E. Barron, J. Org. Chem. 1969, 34,
–1
1
1005–1007; g) W. Reeve, Synthesis 1971, 131–138; h) W. Reeve,
E. R. Barron, J. Org. Chem. 1975, 40, 1917–1920; i) W. Reeve,
R. J. Bianchi, J. R. McKee, J. Org. Chem. 1975, 40, 339–342; j)
W. Reeve, W. R. Coley III, Can. J. Chem. 1979, 57, 444–449; k)
W. Reeve, T. F. Steckel, Can. J. Chem. 1980, 58, 2784–2788; l)
W. Reeve, R. Tsuk, J. Org. Chem. 1980, 45, 5214–5215.
(
(
film): ν˜ = 3337, 2917, 1495, 1453, 1056, 1029 cm . H NMR
CDCl , 500 MHz): δ = 7.27–7.32 (m, 2 H), 7.17–7.24 (m, 3 H),
.93–4.95 (m, 1 H), 4.90–4.92 (m, 1 H), 3.70 (t, J = 6.5 Hz, 2 H),
.38 (s, 2 H), 2.27 (dt, J = 6.5, 0.6 Hz, 2 H), 1.33 (br. s, 1 H) ppm.
3
4
3
1
3
C NMR (CDCl
3
, 125 MHz): δ = 145.4, 139.2, 129.0, 128.4, 126.3,
14O 162.1045,
1
13.8, 60.4, 42.9, 38.6 ppm. HRMS: calcd. for C11
H
[
2] a) P. J. Atkins, V. Gold, R. Marsh, J. Chem. Soc. Perkin Trans.
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found 162.1045.
Preparation of 2-(4-Methoxyphenyl)oxirane: This procedure was
based on the method reported by Tsuchiya, Kumamoto, and Ishi-
[
24]
kawa.
Sodium hydride (240 mg, 6.0 mmol, 60% suspension in
oil) was placed in a dry 25 mL round-bottomed flask equipped
with a magnetic stir bar. Anhydrous DMSO (8 mL) was added fol-
lowed by trimethylsulfonium iodide (1.22 g, 6.0 mmol). This mix-
ture was stirred at room temp. under Ar for 30 min. Then, the
mixture was cooled to 0 °C with an ice bath, and a p-anisaldehyde
3
3, 2233–2244.
3] M. K. Gupta, Z. Li, T. S. Snowden, J. Org. Chem. 2012, 77,
854–4860.
4] a) W. Reeve, R. J. Bianchi, J. R. McKee, J. Org. Chem. 1975, 40,
39–342; b) W. Reeve, J. R. McKee, R. Brown, S. Lakshmanan,
[
[
(0.6 mL, 5.0 mmol) solution in DMSO (1.5 mL) was added. After
4
the addition was complete, the ice bath was removed, and the reac-
tion mixture was stirred at room temp. under Ar for 2 h. The reac-
3
tion was then quenched with H
tracted with EtOAc (3ϫ 50 mL). The combined organic layers were
washed with H O (3ϫ 20 mL) and brine (20 mL), dried with anhy-
2
O (10 mL) and the mixture ex-
G. A. McKee, Can. J. Chem. 1980, 58, 485–493; c) A. V. Mkhit-
aryan, A. A. Avetissyan, Khim. Zh. Arm. 2002, 55, 36–43; d)
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2
drous magnesium sulfate, vacuum-filtered through a fritted funnel,
and concentrated under reduced pressure. The crude material was
purified by Kugelrohr distillation (173 °C, 0.1 mm) to afford
[
5] a) E. J. Corey, J. O. Link, Tetrahedron Lett. 1992, 33, 3431–
3
434; b) E. J. Corey, J. O. Link, J. Am. Chem. Soc. 1992, 114,
600 mg (4.0 mmol, 80% yield) of the 2-(4-methoxyphenyl)oxirane
1906–1908; c) C. Dominguez, J. Ezquerra, S. R. Baker, S. Bor-
relly, L. Prieto, C. M. Espada, C. Pedregal, Tetrahedron Lett.
1998, 39, 9305–9308; d) R. Tennyson, D. Romo, J. Org. Chem.
as a colorless oil. IR (film): ν˜ = 2924, 2837, 1614, 1516, 1245,
–
1 1
1
2
3
2
1
1
3
033 cm . H NMR (CDCl , 500 MHz): δ = 7.20 (d, J = 8.8 Hz,
2000, 65, 7248–7252; e) C. Mellin-Morlière, D. J. Aitken, S. D.
H), 6.89 (d, J = 8.8 Hz, 2 H), 3.82 (dd, J = 4.0, 2.7 Hz, 1 H),
Bull, S. G. Davies, H.-P. Husson, Tetrahedron: Asymmetry
2001, 12, 149–155; f) R. L. Tennyson, G. S. Cortez, H. J. Gal-
icia, C. R. Kreiman, C. M. Thompson, D. Romo, Org. Lett.
.80 (s, 3 H), 3.12 (dd, J = 5.3, 4.0 Hz, 1 H), 2.80 (dd, J = 5.3,
.7 Hz, 1 H) ppm. 1 C NMR (CDCl
3
3
, 125 MHz): δ = 159.6, 129.4,
26.8, 113.9, 55.2, 52.1, 50.9 ppm. HRMS: calcd. for C
50.0681, found 150.0686.
9 10 2
H O
2
002, 4, 533–536; g) T. A. Mitchell, D. Romo, Heterocycles
2
005, 66, 627–637.
[
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Reduction of 2-(4-Methoxyphenyl)oxirane: Freshly prepared 2-(4-
methoxyphenyl)oxirane (75.0 mg, 0.5 mmol) was dissolved in dry
2
2
(
4
-propanol (2 mL). To this solution was added lithium borohydride
one attempt by using 11 mg, 0.5 mmol and another one by using
4 mg, 2.0 mmol). This reaction mixture was heated to 40 °C (oil-
3
1
1
2
596; d) J. E. Oliver, W. F. Schmidt, Tetrahedron: Asymmetry
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bath temperature) and allowed to react under Ar for 12 h, at which
time the reaction was complete as judged by TLC. The reaction
was then quenched with satd. aqueous NH
4
Cl (5 mL), and the
A. H. White, Aust. J. Chem. 2006, 59, 426–433; g) H. Morim-
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aqueous phase was saturated with solid NaCl. The products were
extracted with ethyl acetate (5ϫ 10 mL), dried with anhydrous
magnesium sulfate, vacuum-filtered, and concentrated under re-
duced pressure. Products 7 and 8 were generated in a 0.9:1 ratio
3
146–3150; Angew. Chem. 2006, 118, 3218; h) J. L. Shamshina,
T. S. Snowden, Org. Lett. 2006, 8, 5881–5884; i) L. R. Cafiero,
T. S. Snowden, Org. Lett. 2008, 10, 3853–3856; j) A. Ganta,
L. R. Cafiero, J. L. Shamshina, T. S. Snowden, Tetrahedron
(
4
by using 1.0 equiv. of LiBH
4
) and in a 1.4:1 ratio (by using
.0 equiv. of LiBH
4
), as determined by 1H NMR spectra of the
2
012, 68, 5396–5405; k) M. S. Perryman, M. E. Harris, J. L.
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crude product mixtures.
(
Li, T. S. Snowden, Org. Lett. 2014, 16, 1602–1605; m) M. S.
Perryman, M. W. M. Earl, S. Greatorex, G. J. Clarkson, D. J.
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Acknowledgments
We gratefully acknowledge the National Science Foundation
CAREER program (CHE-0847686) for financial support. We also
thank Dr. Qiaoli Liang for assistance with mass spectrometry stud-
ies and Margaret Tebbs for her help in preparing compound series
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7018
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