Chloromethyl Methyl Ether → HCID 18970132, compound

Participants

Reaction Steps

To a solution of 1.96 g (6.16 mmol) of 5-Hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol in 10 mL of anhy. DMF (Aldrich) under argon at RT was added 260 mg (~1.05 eq.) of a 60% dispersion of sodium hydride (Aldrich) and the mixture stirred at RT under argon until effervescence had ceased and the solution had become a clear, darker colored solution. To the stirred solution was added 0.55 mL (~1 eq.) of methoxymethyl chloride (Aldrich, 85% purity technical grade) by syringe directly into the solution with the needle tip below the surface of the solution. The color of the reaction mixture discharged and a precipitate formed within 1 min. Stirring was continued for 0.5 hr. Half of the solution was then withdrawn by syringe for use in another reaction. The remaining half was poured into a mixture of 50 mL of sat. aq. NaHCO3 and 100 mL EtOAc, the mixture shaken well and sufficient water added to dissolve solids that formed to give two clear phases. The phases were separated and the organic phase washed with half-sat. aq. NaCl (2×50 mL), sat. aq. NaCl (1×50 mL), dried (Na2SO4), evaporated under reduced pressure and the residue dried under high vacuum to give 1.05 g (~94%) of the desired product 5-(Methoxymethoxy)-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol as an oil, shown by 1H-NMR to be of good purity.

Provenance & Evidence