1836
S. SINGHAL, S. L. JAIN, AND B. SAIN
General Procedure for MPHT-Catalyzed Nucleophilic Ring Opening
with Alcohols, Water, Acetic Anhydride, and Amines
Nucleophile (2 mmol) was added into a stirred mixture of an epoxide (1 mmol)
and MPHT (10 mol%) in a 50-ml round-bottomed flask, and the reaction continued
at room temperature for the appropriate time as mentioned in Tables 2 and 3. After
completion of the reaction as indicated by thin-layer chromatography (TLC), the
reaction mixture was quenched with water and extracted with dichloromethane
(3 Â 10 ml). The combined organic layer was dried over anhydrous Na2SO4 and con-
centrated under vacuum. The crude product was purified by flash chromatography
to yield pure b-hydroxy product.
ACKNOWLEDGMENTS
We are grateful to the director, Indian Institute of Petroleum, for his kind
permission to publish these results. S. L. J. and S. S. are thankful to the Council
of Scientific and Industrial Research New Delhi, for the award of research
fellowships.
REFERENCES
1. Parker, R. E.; Isaacs, N. S. Mechanisms of epoxide reactions. Chem. Rev. 1959, 59,
737–799.
2. Bonini, C.; Righi, G. Regio- and chemoselective synthesis of halo-hydrins by cleavage of
oxiranes with metal halides. Synthesis 1994, 225–238.
3. Yadav, J. S.; Ramesh Reddya, A.; Venkat Narsaiaha, A.; Reddy, B. V. S. An efficient
protocol for regioselective ring opening of epoxides using samarium triflate: Synthesis
of propranolol, atenolol, and RO363. J. Mol. Catal. A: Chem. 2007, 261, 207–212.
4. Das, B.; Reddy, V. S.; Tehseen, F. A mild, rapid, and highly regioselective ring-opening of
epoxides and aziridines with acetic anhydride under solvent-free conditions using
ammonium-12-molybdophosphate. Tetrahedron Lett. 2006, 47, 6865–6868.
5. Yadav, J. S.; Reddy, B. V. S.; Harikishan, K.; Narsaiah, M. A. V. Carbon tetrabromide:
An efficient catalyst for regioselective ring opening of epoxides with alcohols and water.
Synthesis 2005, 2897–2890, and references cited therein.
6. Iranpoor, N.; Salehi, P. Highly efficient regio- and stereoselective alcoholysis of epoxides
catalyzed with iron(III) chloride. Synthesis 1994, 1152–1154.
7. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Fard, M. A. B. Silica sulfuric acid: An efficient and
reusable catalyst for regioselective ring opening of epoxides by alcohols and water.
Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 1113–1121.
8. Firouzabadi, H.; Iranpoor, N.; Khoshnood, A. Aluminum tris (dodecyl sulfate) trihydrate
Al(DS)3 Á 3H2O as an efficient Lewis acid–surfactant combined catalyst for organic reac-
tions in water: Efficient conversion of epoxides to thiiranes and to amino alcohols at room
temperature. J. Mol. Catal A: Chem. 2007, 274, 109–115.
9. Vijender, M.; Kishore, P.; Narender, P.; Satyanarayana, B. Amberlist-15 as heterogeneous
reusable catalyst for regioselective ring opening of epoxides with amines under mild
conditions. J. Mol. Catal. A: Chem. 2007, 266, 290–293.
10. Kamal, A.; Ramu, R.; Azhar, M. A.; Khanna, G. B. R. Copper(II) tetrafluoroborate–
catalyzed ring opening of epoxides by amines. Tetrahedron Lett. 2005, 46, 2675–2677.