Methyl morpholine oxide → Ethyl 4-isobutyrylbenzoate

Participants

Reaction Steps

To a solution of 2.08 g (9.36 mmol) of ethyl 4-(1-hydroxy-2-methylpropyl)benzoate (from Step A) and 1.64 g (14.04 mmol) of 4-methylmorpholine N-oxide in 20 mL of CH2Cl2 were added 164 mg (0.47 mmol) of tetrapropylammonium perruthenate and few specks of ground 4 A molecular sieves. After stirring at rt for 2 h, the mixture was filtered through a cake of Celite and the filtrate was concentrated. Chromatography on a Biotage 40M cartridge using 1:19 v/v EtOAc/hexanes as the eluant gave 2.0 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.23 (t, J=6.9, 6H), 1.41 (t, J=7.1, 3H), 3.56 (m, 1H), 4.41 (q, J=7.1, 2H), 7.99 (dd, J=1.7, 6.5, 2H), 8.13 (dd, J=1.9, 6.7, 2H).

Provenance & Evidence