Chloromethyl Methyl Ether → HCID 10494728, compound

Participants

Reaction Steps

Compound C (8.26 g, 31.65 mmol) and DIPEA (57.2 mL, 317.7 mmol) were dissolved in 160 mL of methylene chloride. The mixture was cooled in an ice-water bath and stirred under N2. Methoxymethyl chloride (12.2 mL, 159 mmol) was added dropwise. After the addition, the mixture was stirred at room temperature under N2 overnight. The mixture was diluted with 140 mL of methylene chloride and washed with 10% HCl solution (2×50 mL) and water (3×50 mL) and dried over MgSO4. Filtration and solvent evaporation gave a yellow residue, which was purified on a silica gel column (hexanes and ethyl acetate, 3/1, v/v) to give 8.61 g (87%) of a solid product. 1H NMR (CDCl3) δ5.96 (m, 1H), 5.07-4.95 (m, 2H), 4.90 (s, 2H), 3.63 (s, 3H), 3.47 (d, J=5.7 Hz, 2H), 2.58 (s, 2H), 2.40 (s, 3H), 2.22 (s, 3H), 1.47 (s, 6H).

Provenance & Evidence