Pyridine → HCID 119083722, compound

Participants

Reaction Conditions

Reaction Steps

21 (rac-Ethyl (2E)-4-hydroxypent-2-enoate) (crude, HPLC: ˜94 area %, 9.20 g, 60 mmol), pyridine (9.7 ml, 0.12 mol) and DMAP (1.47 g, 12 mmol) are dissolved in THF (300 ml) and cooled to 0° C. Chloroacetylchloride (9.6 ml, 0.12 mol) in THF (60 ml) is added dropwise under stirring at ≦2° C. over 10 min. The reaction mixture is stirred 40 min at 0° C. The resulting suspension is then poured onto H2O (250 ml) and extracted with tBuOMe (1 l). The organic phase is washed with saturated NaHCO3 (100 ml), 1 M HCl (100 ml), H2O (3×100 ml) and brine (100 ml) successively. The organic phase is dried with Na2SO4 and evaporated under reduced pressure at 40° C. The residue is purified by HPLC (tBuOMe:hexane fraction 5:95) and yields 30 (rac-Ethyl (2E)-4-(chloroacetoxy)pent-2-enoate) (9.81 g, 74%) as a yellowish oil.

Provenance & Evidence