Sodium hydride → HCID 59253200, compound

Participants

Reaction Steps

Sodium hydride (60% wt in oil) (3.14 g, 78 mmol) was added to a stirred solution of methyl 3-hydroxy-2,2-dimethylpropanoate (5 mL, 39.2 mmol) in DMF (5.6 mL) at 0° C., after 5 min 1-bromo-2-methoxyethane (7.4 mL, 78 mmol) was added dropwise, and the reaction mixture was allowed to stir for 3 h. The reaction was quenched with sat. NH4Cl (aq.) (30 mL) and the aqueous layer was extracted with DCM (2×50 mL), the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude oil was dissolved in EtOAc (125 mL) and washed with water (3×40 mL), dried (MgSO4), filtered and concentrated in vacuo. The material was purified by vacuum distillation (68-69° C., 4.4 mbar) to afford methyl 3-(2-methoxyethoxy)-2,2-dimethylpropanoate (39) (1.83 g, 25%) as a colourless oil: 1H NMR (400 MHz, CDCl3) δ: 3.68 (s, 3H), 3.60-3.58 (m, 2H), 3.52-3.50 (m, 2H), 3.49 (s, 2H), 3.37 (s, 3H), 1.19 (s, 6H).

Provenance & Evidence