Sodium Iodide → 2-Methyl-2-(2-methyl-4-pent-4-ynyloxy-phenoxy)-propionic acid ethyl ester

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Reaction Steps

To a solution of 0.95 g (4.0 mmol) 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 0.42 ml (4.0 mmol) 5-chloro-pent-1-yne in 20 ml acetonitrile were added 0.60 g (4.0 mmol) NaI and 1.56 g (4.80 mmol) Cs2CO3. The mixture was stirred at 50° C. for 3 days and every day 0.42 ml (4.0 mmol) 5-chloro-pent-1-yne and 1.56 g (4.80 mmol) Cs2CO3 were added (two times). After 2 further days stirring at ambient temperature and filtration, the solvent was evaporated. The residue was redissolved in dichloromethane, dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (SiO2, n-heptane/EtOAc 2.5 to 5%) yielded 1.11 g of the title compound as colorless oil.

Provenance & Evidence