Methyl iodide → Methyl 2-methoxy-2-methylpropanoate

Participants

Reaction Conditions

Reaction Steps

A 0° C. solution of methyl 2-hydroxyisobutyrate (2 g, 16.93 mmol) in DMF (20 mL) was treated with NaH (60% in mineral oil, 0.813 g, 20.33 mmol), stirred for 0.5 h at 0° C., treated with iodomethane (1.269 mL, 20.29 mmol), allowed to warm to RT and stirred overnight. The mixture was diluted with EtOAc, quenched with cold satd. NH4Cl, extracted with EtOAc (3×) and the combined organics were washed with satd. NaHCO3, 10% LiCl, then brine, dried over Na2SO4 and concentrated to dryness to afford methyl 2-methoxy-2-methylpropanoate (2.08 g, 93%). 1H NMR (400 MHz, DMSO-d6): δ 3.64 (s, 3H), 3.11 (s, 3H), 1.30 (s, 6H).

Provenance & Evidence