Methyl 3-hydroxypivalate → Methyl 2,2-dimethyl-3-oxopropanoate

Participants

Reaction Steps

Add methyl 3-hydroxy-2,2-dimethylpropanoate (33 g, 250 mmol) to Dess-Martin periodinane (106 g, 250 mmol) suspended in DCM (1000 mL) at 0° C. and stir at room temperature for 18 h. Filter the reaction mixture through a celite bed and concentrate the filtrate. Wash the concentrated filtrate with pentane (2×200 mL). Separate the pentane layer and concentrate in vacuo to give methyl 2,2-dimethyl-3-oxo-propanoate (31.93 g, quantitative). 1H NMR (d6-DMSO) δ 9.59 (s, 1H), 3.67 (s, 3H), 1.26 (s, 6H).

Provenance & Evidence