1,3-Propanediol → HCID 131720726, compound

Participants

Reaction Steps

DEAD (0.14 g, 0.00079 mol) was added to a solution of acid 23 (0.3 g, 0.00079 mol) dissolved in anhydrous THF (10 mL). A mixture of triphenylphosphine (0.21 g, 0.0008 mol) and 1,3-propanediol (0.091 g, 0.0011 mol) in THF (3 mL) was injected slowly to the above solution and reaction mixture stirred at room temperature for 24 hours. The solution was quenched with H2O (12 mL) and extracted with ethyl acetate (2×15 mL). The organic layer was dried over anhydrous Na2 SO4 and concentrated under reduced pressure. Purification by preparative TLC (ethylacetate/hexane, 70:30) gave the pure ester (24) (0.25 g, 0.00058 mol, 73%). 1H NMR (CDCl3) δ 1.11 (S, 9H), 1.88-1.96 (m, 2H), 2.49 (bs, 1H), 3.67 (t, 2H, J=6 Hz), 4.38 (t, 2H, J=6Hz), 6.86-7.72 (m, 14H). M.S. Exact mass: calculated 434.4126, found M+1, 435.

Provenance & Evidence