Iodoethane → HCID 22395030, compound

Participants

Reaction Conditions

Reaction Steps

A 0° C. suspension of NaH (60% wt. in mineral oil, 1.4 g, 35.0 mmol) in DMF (11 mL) under Ar was treated drop-wise with a solution of methyl 2-hydroxyisobutyrate (2.0 g, 16.93 mmol) in THF (5 mL), stirred at 0° C. for 0.5 h, allowed to warm to RT, and stirred for 0.5 h. The mixture was re-cooled to 0° C., treated drop-wise with iodoethane (6.0 g, 35.3 mmol) and stirred overnight as the cooling bath expired. The mixture was diluted with water, extracted with Et2O (5×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford methyl 2-ethoxy-2-methylpropanoate (1.6 g, 65%) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 3.63 (s, 3H), 3.31 (q, J=7.0 Hz, 2H), 1.30 (s, 6H), 1.06 (t, J=7.0 Hz, 3H).

Provenance & Evidence