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Synlett 2013; 24(2): 236-240
DOI: 10.1055/s-0032-1317965
DOI: 10.1055/s-0032-1317965
letter
A Simple and Efficient Method for One-Pot, Three-Component Synthesis of Terminal Vinylphosphonates Using a Task-Specific Ionic Liquid
Authors
Further Information
Publication History
Received: 13 November 2012
Accepted after revision: 11 December 2012
Publication Date:
03 January 2013 (online)
Abstract
A convenient and practical method for the one-pot, three-component synthesis of terminal vinylphosphonates from readily available starting materials (aryl/alkyl/heteroaryl aldehydes, nitromethane and trialkylphosphites) through a tandem Henry–Michael reaction followed by nitro elimination in the presence of 5-hydroxypentylammonium acetate (5-HPAA) as a task-specific ionic liquid, is described. This method offers several advantages such as the use of a reusable and inexpensive ionic liquid, which is an environmentally benign reaction medium, and a simple reaction setup that does not require specialized equipment. The approach offers good yields of the products under mild reaction conditions.
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- 13 Three-Component, One-Pot Synthesis of Vinylphosphonates; General Procedure: 5-HPAA (0.5 mL) was added to a stirred mixture of aldehyde (1 mmol), nitromethane (1 mmol) and trialkylphosphite (1 mmol) at r.t. After stirring for the appropriate time (Table 2), H2O (10 mL) was added and the reaction mixture was extracted with EtOAc (3 × 10 mL). The combined organic layers were dried over Na2SO4 and filtered. Evaporation of the filtrate produced an almost pure product, which was purified further by chromatography on silica (n-hexane–EtOAc, 1:2). The separated aqueous layer containing 5-HPAA was evaporated, dried under reduced pressure at 100 °C for 24 h and reused in subsequent reactions.