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I. Yavari et al.
round-bottomed flask was added with stirring a mixture of methyl
4-sulfanylbutanoate (20 mmol) in CH2Cl2 (30 mL). The reaction mix-
ture was stirred at r.t. until the yellow color of the complex disappeared.
The organic layer (Solution A) was separated, the remaining aqueous
layer was washed twice with 20-mL portions of CH2Cl2, and the wash-
ings were added to the organic layer. The CH2Cl2 solution was washed
successively with diluted (1%) aqueous HCl, water, diluted (3%) aque-
ous sodium carbonate, and water. The dried (MgSO4) solution was con-
centrated to afford 10, which was of good purity without further purifi-
cation needed. IR (KBr) υmax (cm−1): 1730 (C=O), 1428, 1354, 1011. 1H
NMR (CDCl3) δ = 1.35–1.39 (4 H, m, CH2), 2.81–3.00 (8 H, m, OCH2
and SCH2), 4.03 (6 H, s, OMe). - 13C NMR (CDCl3): δ = 29.3 (CH2), 32.8
(OCH2), 33.6 (SCH2), 51.6 (OMe), 172.4 (C=O) ppm.
Accordingly, compounds 1–9 were prepared in 92–98% yields (see
Table I). 1H and 13C NMR spectra of the crude reaction mixtures clearly
indicated the formation of the disulfides. Any product other than disul-
fides could not be detected by NMR spectroscopy.
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