Mild and efficient method for oxathioacetalization of carbonyl compounds

Article abstract of DOI:10.1080/00397910600947783

An efficient procedure for the protection of carbonyl compounds into the corresponding 1,3-oxathioacetal has been achieved using PAS as catalyst. Copyright Taylor & Francis Group, LLC.

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Mild and Efficient Method for
Oxathioacetalization of Carbonyl Compounds
Adinath Majee a , Shrishnu Kumar Kundu a & Samimul Islam a
a Department of Chemistry , Visva‐Bharati University , Santiniketan, West
Bengal, India
Published online: 01 Dec 2006.
To cite this article: Adinath Majee , Shrishnu Kumar Kundu & Samimul Islam (2006) Mild and Efficient Method
for Oxathioacetalization of Carbonyl Compounds, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 36:24, 3767-3770, DOI: 10.1080/00397910600947783
To link to this article: http://dx.doi.org/10.1080/00397910600947783
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Synthetic Communicationsw, 36: 3767–3770, 2006
Copyright # Taylor & Francis Group, LLC
ISSN 0039-7911 print/1532-2432 online
DOI: 10.1080/00397910600947783
Mild and Efficient Method
for Oxathioacetalization
of Carbonyl Compounds
Adinath Majee, Shrishnu Kumar Kundu, and Samimul Islam
Department of Chemistry, Visva-Bharati University, Santiniketan,
West Bengal, India
Abstract: An efficient procedure for the protection of carbonyl compounds into the
corresponding 1,3-oxathioacetal has been achieved using PAS as catalyst.
Keywords: 2-Marcaptoethanol, PAS, protection
INTRODUCTION
Oxathioacetals are prepared from the corresponding carbonyl compounds by
reaction with 2-marcaptoethanol by an equimolar amount of Lewis acid
such as BF3 OEt2 and ZnCl2.[2] Other methods in the literature employ
[1]
.
TMSOTf,[3] ZrCl4,[4] LiBF4,[5] HClO4,[6] OTAB,[7] NBS,[8] Sc(OTf)3,[9]
In(OTf)3,[10] TBAB,[11] and Me2SþBrBr2[12] as catalysts. We have
observed that carbonyl compounds and 2-marcaptoethanol react con-
veniently in the presence of polyaniline sulphate salt (PAS) as a catalyst
to give the corresponding 1,3-oxathiolanes in good yields Scheme 1.
The results are shown in Table 1.
In a typical reaction procedure, the carbonyl compound (1 mmol), 2-mar-
captoethanol (1.2 mmol), and a catalytic amount of PAS (0.01 mmol) in
dichloromethane (3 mL) were stirred at room temperature as required for
Received in India May 4, 2006
Address correspondence to Adinath Majee, Department of Chemistry, Visva-
Bharati University, Santiniketan, West Bengal 731235, India. E-mail: adinathm@
yahoo.com
3767

3768
A. Majee, S. K. Kundu, and S. Islam
Scheme 1.
Table 1. Preparation of oxathioacetals from the carbonyl compounds
Time
(h)
Yield
(%)a
Entry
1
Substrate
Product
3
72
2
5
60
3
4
5
4
4
4
60
70
65
6
7
2
4
75
70
8
9
6
4
65
75
(continued)

Carbonyl Compounds
3769
Table 1. Continued
Time
(h)
Yield
(%)a
Entry
10
Substrate
Product
6
4.5
4
60
65
60
11
12
1
aYields are pure isolated product, characterized by IR and H NMR.
completion as monitored by thin-layer chromatography, (TLC). Evaporation
of the solvent from the reaction mixture under reduced pressure gives the
crude product. The pure product is obtained by column chromatography.
ACKNOWLEDGMENT
We are thankful to the Department of Chemistry, Visva-Bharati university and
the DST-FIST program. We also express our sincere thanks to B. C. Ranu,
HOD, Department of Chemistry, Indian Association for the Cultivation of
Science, for his constant encouragement.
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