Acetic acid methanol → HCID 131715536, compound

Participants

Reaction Steps

To a solution of acetate (V) (20.6 g, 4.46 mmol) in a 1:1 solution of MeOH/HOAc (100 ml) was added 2.0 g of 10% Pd/C and 82 μl of pyridine (0.4%). The solution was shaken on a Parr apparatus under 50 psig of H2. After 24 h the solution was filtered and concentrated, and the residue was purified on a Waters Prep-500 HPLC (EtOAc/hexane, 22/78) to yield 6.4 g of a light yellow oil (39%), homogeneous by TLC. This reaction routinely gave yields of 35-40%. The point at which the reaction is removed from the hydrogenator is determined by when the selectively reduced compound appears greatest by TLC analysis. 1H NMR (CDCl3)δ: 7.3 (s, 10H), 6.2 (br s, 1H), 3.6-4.7 (m, 9H), 2.10 (s, 3H). 13C NMR (CDCl3) δ: 169.9, 137.5, 137.1, 128.5 (4C), 128.0 (4C), 127.7 (2C), 100.4 (αC-1), 86.8, 84.6, 82.8, 72.4, 72.1, 62.1, 21.2 Elemental Analysis: Calculated for C21H24O6 : C, 67.73; H, 6.50. Found: C, 67.49; H, 6.50.

Provenance & Evidence