A Simple and Efficient Method for One-Pot, Three-Component Synthesis of Terminal Vinylphosphonates Using a Task-Specific Ionic Liquid

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.

Key words

phosphonate - multicomponent reaction - phosphite ­esters - ionic liquids - aldehydes

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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.