Tetrahydrofuran → N-(2,4,6-trimethoxybenzyl)-2-azetidinone

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Reaction Steps

In a 50 ml round bottom 3-neck flask was prepared a solution of 1.2 mmol lithium diisopropylamide in ca. 10 ml tetrahydrofuran. To this clear, practically colorless solution cooled to -78°, was added 0.34 g (1 mmol) N-(2,4,6-trimethoxybenzyl)-2-carbo-tert-butoxyazetidine dissolved in 3 ml tetrahydrofuran. After stirring for 1 hour at this temperature, the golden-orange solution was silylated and photooxygenated in the usual manner. The resulting pink solution was then concentrated in vacuo and the residue applied to a 10×2 cm silica gel (Woelm) column. Elution with chloroform gave 0.14 g (56%) of pale yellow liquid, which by NMR analysis was greater than 90% pure: IR (liquid film) cm-1 1745, 1600, 1230, 1210, 1150, 1060, 1050, 950, 820; NMR (CDCl3) delta 6.09 (2H, s), 4.36 (2H, s), 3.79 (6H, s), 3.75 (3H, s), 2.98 (2H, t, J=4 Hz), 2.74 (2H, t, J=4 Hz).

Provenance & Evidence