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Synlett 2010(7): 1047-1050  
DOI: 10.1055/s-0029-1219577
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

The First One-Pot Synthesis of Morita-Baylis-Hillman Adducts Starting Directly from Alcohols

Lal Dhar Singh Yadav*, Vishnu Prabhakar Srivastava, Rajesh Patel
Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211002, India
Fax: +91(532)2460533; e-Mail: ldsyadav@hotmail.com;
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Publikationsverlauf

Received 5 January 2010
Publikationsdatum:
10. März 2010 (online)

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Abstract

The first example of one-pot oxidative carbon-carbon bond formation via the Morita-Baylis-Hillman reaction using alcohols is reported. The protocol involves silica gel-DABCO catalyzed oxidation of alcohols to aldehydes with chloramine-T followed by their Morita-Baylis-Hillman reaction with acrylonitrile or methyl acrylate to give 70-87% overall yields of the corresponding ­Morita-Baylis-Hillman adducts. The present work opens up a new and efficient synthetic route to Morita-Baylis-Hillman adducts directly from alcohols in a one-pot operation.

Key words

oxidation - C-C bond formation - alcohols - chloramine-T - silica gel-DABCO - Morita-Baylis-Hillman adducts

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22

General Procedure for the Synthesis of MBH Adducts 6
A mixture of alcohol 1 (5 mmol), chloramine-T (2, 5 mmol), DABCO (5 mmol), and SiO2 (200 mg) in 1,4-dioxane-H2O (3 mL, 1:1) was stirred at r.t. until the chloramine-T was consumed (6-24 h), then acrylonitrile or methyl acrylate (15 mmol) was added and the mixture was stirred at r.t. for 5-45 h (Table  [²] ).The reaction progress was monitored by TLC. Upon completion, the reaction mixture was evaporated under reduced pressure and extracted with EtOAc (3 × 5 mL). The combined organic phase was dried over MgSO4, filtered, and evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using hexane-EtOAc as eluent to give pure products 6. The structure of the products was confirmed by comparison of their mp or bp, TLC, IR, and NMR data with authentic samples prepared by literature methods.4j,n,o,q,²³