tert-Butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate → tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)-2,2-dimethylpropanoate

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Reaction Steps

A suspension of tert-butyl 3-(2-(2-(benzyloxy)ethoxy)ethoxy)-2,2-dimethylpropanoate (48) (13 g, 37 mmol) and 10% Pd/C (1.3 g) in EtOH (92 mL) were placed under 5 bar of H2 pressure (isolated system), and stirred for 16 h. The mixture was filtered through celite and the filtrate concentrated in vacuo to afford tert-butyl 3-(2-(2-hydroxyethoxy)ethoxy)-2,2-dimethylpropanoate (49) (8.2 g, 85%) as a colourless oil: m/z 285 (M+Na)+ (ES+). 1H NMR (400 MHz, CDCl3) δ: 3.73-3.69 (m, 2H), 3.66-3.58 (m, 6H), 3.44 (s, 2H), 2.37 (t, J=6.2 Hz, 1H), 1.43 (s, 9H), 1.14 (s, 6H).

Provenance & Evidence