Pyridine → HCID 219358, compound

Participants

Reaction Steps

Combine methyl chloroformate (7.04 g, 80.0 mmol) in THF (70 mL) and add dropwise to a ice-water cold solution of 2-buten-1,4-diol (majority Z form) (19.7 g, 208 mmol) and pyridine (16.5 g, 208 mmol) in THF (150 mL). Warm the mixture to room temperature and stir for 20 hours. Remove the pyridine salt by filtration and concentrate the filtrate to a residue. Dissolve the residue with CH2Cl2 and wash sequentially with 1 N HCl and brine. Dry the organic layer over Na2SO4 and concentrate the solvent in vacuo to give a residue. Purification by chromatography using hexanes: EtOAc=12:1 as the eluents give the title compound: 1H NMR (CDCl3): δ5.82–5.79 (m, 2H), 4.75 (d, J=4.8 Hz, 4H), 3.79 (s, 6H).

Provenance & Evidence