Job/Unit: O50156
/KAP1
Date: 20-03-15 11:26:45
Pages: 8
H. Firouzabadi, N. Iranpoor, F. Gorginpour, A. Samadi
FULL PAPER
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combined organic phases were dried with Na2SO4, filtered, and
concentrated to yield the crude product, which was further purified
by column chromatography on silica gel (petroleum ether) to pro-
vide 1,2-diheptyl sulfide (1d, 90% yield) as a colorless oil. 1H NMR
(250 MHz, CDCl3): δ = 2.43 (t, J = 7 Hz, 4 H), 1.56–1.47 (m, 4
H), 1.26–1.21 (m, 16 H), 0.8 (t, J = 6.5 Hz, 6 H) ppm. 13C NMR
(62.5 MHz, CDCl3): δ = 32.1, 31.7, 29.7, 28.9, 22.5, 14.0 ppm.
Synthesis of Diphenyl Sulfide as a Typical Procedure (2a): To a glass
tube that contained CuI (0.028 g, 15 mol-%), K2CO3 (0.276 g,
2 mmol), and dithiooxamide (0.12 g, 1 mmol) in wet PEG200
(0.15 mL of H2O in 2 mL PEG200) was added iodobenzene
(0.11 mL, 1 mmol). The glass tube was sealed under vacuum,
placed in an oil bath at 120 °C, and stirred for the appropriate
reaction time (6 h for 2a). Upon completion of the reaction, the
tube was cooled to room temperature and then opened. The reac-
tion mixture was diluted with H2O (5 mL), and the resulting mix-
ture was extracted with EtOAc (4ϫ 10 mL). The combined extracts
were dried anhydrous Na2SO4 and concentrated. The crude organic
product was purified by column chromatography on silica gel (pe-
troleum ether) to give diphenyl sulfide (2a, 95% yield) as a yellow
oil. 1H NMR (250 MHz, CDCl3): δ = 7.44–7.05 (m, 10 H) ppm.
13C NMR (62.5 MHz, CDCl3): δ = 137.0, 129.1, 127.5, 127.1 ppm.
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Synthesis of 4-(Benzylthio)butan-2-one (3a) as a Typical Procedure
for Thia-Michael Adduct Formation: A mixture of benzyl bromide
(0.12 mL, 1 mmol), dithiooxamide (0.12 g, 1 mmol), and PEG200
(2 mL) was heated at 80 °C for 30 min. NaHCO3 (0.126 g,
1.5 mmol) and methyl vinyl ketone (0.084 mL, 1 mmol) were added
to mixture, which was then heated at 50 °C for 30 min. The mixture
was diluted with water (3 mL), and the resulting mixture was ex-
tracted with ethyl acetate (3ϫ 3 mL). The combined extracts were
dried and concentrated to give the crude residue, which was further
purified by silica gel chromatography (petroleum ether/EtOAc,
10:1) to provide 4-(benzylthio)butan-2-one (3a, 85% yield) as a
colorless oil. 1H NMR (250 MHz, CDCl3): δ = 7.31–7.21 (m, 5 H),
3.71 (s, 2 H), 2.69–2.59 (m, 4 H), 2.10 (s, 3 H) ppm. 13C NMR
(62.9 MHz, CDCl3): δ = 206.7, 138.2, 128.8, 128.5, 127.0, 43.2,
36.6, 30.0, 25.1 ppm.
Acknowledgments
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The authors thank the National Elite Foundation of Iran for a
grant (BN048) and also the Shiraz University Research Council for
support of this work.
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