Pyridine → Triethylammonium 2-[2-(4,4'-dimethoxytrityloxy)ethoxy] acetate

Participants

Reaction Steps

A solution of 2-(2-hydroxyethoxy)acetic acid prepared as desctibed in (Snapp, Thomas C., Jr.; Blood, Alden E. Ether diester derivatives of p-dioxanone. U.S. (1975), 4 pp. U.S. Pat. No. 3,929,847) (7.45 g, 22 mmol) in pyridine (20 mL) is treated with 4,4′-dimethoxytrityl chloride (10.16 g, 30 mmol) overnight at room temperature and concentrated to an oil in vacuo. The residue is dissolved in a mixture of MeOH and CH2Cl2 (95:5, v/v; 200 mL) and washed with 2 M aqueous triethylammonium acetate (5×20 mL). The organic solution is evaporated, re-dissolved in CH2Cl2, dried over Na2SO4, and evaporated to give crude triethylammonium 2-[2-(4,4′-dimethoxytrityloxy) ethoxy] acetate in quantitative yield (10.47 g).

Provenance & Evidence