Acrylic Acid → 5-(Tetrahydro-pyran-2-yloxy)-pent-2-enoic acid

関与物質

反応手順

In a 500 ml rb flask were placed acrylic acid (2.85 g, 39.6 mmol) and Grubbs catalyst (1.68 g, 1.98 mmol) in anhydrous dichloromethane (200 ml). To this solution was added 2-but-3-enyloxy-tetrahydro-pyran (7.73 g, 49.50 mmol) and heated at refluxing for 12 hrs. The solvent was removed and the residue was purified on the column with Hexane/Ethyl acetate=100/5 to remove unchanged 2-but-3-enyloxy-tetrahydro-pyran. Then the column was eluted with Ethyl acetate/Methanol=100/1 to provide 6.66 g of a black oil (84%). 1H-NMR (DMSO-d6) δ 12.190 (s, 1H), 6.845-6.771 (m, 1H), 5.846-5.800 (d, 1H), 4.565-4.548 (t, 1H), 3.739-3.674 (m, 2H), 3.468-3.398 (m, 2H), 2.481-2.395 (m, 2H), 1.689-1.609 (m, 2H), 1.501-1.259 (m, 4H).

情報源と証拠