2,6-Lutidine → HCID 18753697, compound

Participants

Reaction Steps

To a stirred solution of 4-hydroxy-cyclopent-2-enyloxy acetate (4.1 g, 29 mmol) in CH2Cl2 (35 mL) and 2,6-lutidine (8.2 mL, 67 mmol) was added t-butyldimethylsilyl trifluoromethanesulfonate (10 mL, 44 mmol) at 0-5° C. The reaction mixture was stirred at r.t. for 1 hour. It was diluted with CH2Cl2, washed (brine), dried (Na2SO4), filtered and concentrated Column chromatography (silica gel, 5:1 hexanes:diethylether) gave desired product (5.1 g, 69%). 1H NMR (CDCl3, 400 MHz) δ; 5.88 (m, 1H); 5.84 (m, 1H); 5.42 (t, 1H); 4.64 (t, 1H); 2.80 (m, 1H); 2.02 (s, 3H); 1.59 (m, 1H); 0.83 (s, 9H); 0.04 (s, 6H).

Provenance & Evidence