2,2-Dimethoxypropane → HCID 11645721, compound

Participants

Reaction Steps

To a solution of (2R,3S)-2-[3-(4-ethoxyphenyl)propyl]-3-hydroxybutanedioic acid (3.06 g; 10.33 mmol; 1.0 eq.) in acetone (50.0 mL) was added 2,2-dimethoxypropane (1.8 g; 17.6 mmol; 1.7 eq.) and copper(II) chloride (135 mg; 1.03 mmol; 0.1 eq.). The resulting reaction mixture was stirred for 14 h at RT. The reaction mixture was evaporated and the residue taken up in Et2O. Filtration on a pad of celite gave the title product as a greenish oil used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ 7.05 (d, J=8.6 Hz, 2H), 6.80 (d, J=8.6 Hz, 2H), 4.48 d (J=5.0 Hz, 1H), 3.98 (q, J=7.0 Hz, 2H), 3.10-2.81 (m, 1H), 2.74-2.41 (m, 3H), 220-1.15 (m, 4H), 1.61 (s, 3H), 1.50 (s, 3H), 1.35 (t, J=7.0 Hz, 3H).

Provenance & Evidence