Sodium hydride → Methyl(2-(2-allyloxy-ethoxy)-ethoxy)-acetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of alcohol (9) (4.86 g, 33.2 mmol, 1.0 equiv.) in THF (70 mL) was carefully added NaH (60%, 1.60 g, 40.0 mmol, 1.2 equiv.) in small portions at room temperature. The reaction was then refluxed for 1 h (until H2 release ceased) then cooled to 0° C. Methyl bromoacetate (3.8 mL, 40.1 mmol, 1.2 equiv.) was then added dropwise. After 15 min at 0° C., the reaction was submitted to a EtOAc/H2O extraction. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered then evaporated under reduced pressure. Purification was achieved by distillation under high vacuum and provided 4.68 g (64%) of ester (14) as a colourless oil; bp=130-140 0° C. (0.09 Torr); 1H NMR (300 MHz, CDCl3) δ 5.91 (m, 1H), 5.28 (m, 1H), 5.18 (m, 1H), 4.17 (s, 2H), 4.02 (m, 2H), 3.75 (s, 3H), 3.75-3.58 (m, 8H); 13C NMR (75 MHz, CDCl3) δ 171.0, 134.8, 117.1, 72.3, 71.0, 70.8, 70.7, 69.5, 68.7, 51.8; IR (neat) 1754 cm−1; HRMS (ESI, m/z) calcd. for C10H19O5 (MH+) 219.1236, found 219.1227.

Provenance & Evidence