Diethyl Ether → HCID 67415336, compound

Participants

Reaction Steps

Sodium hydride (1.80 g, 45.0 mmol, 60% dispersion in mineral oil) was added slowly to a solution of 1,1-dimethoxypropan-2-ol (2.16 g, 18.0 mmol) (Prepared according to the method described by Hunter et al. Tetrahedron, 1994, 50, 871-888.) in DMF (25 mL) immersed in an ice bath. After the addition was complete, the ice bath was removed to allow the solution to warm to r.t. Then the reaction flask was placed in an ice bath and 2-picolylchloride hydrochloride (2.95 g, 18.0 mmol) was slowly added. After warming to r.t. overnight, diethyl ether, water and brine were added. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by silica gel column chromatography (hexanes/ethyl acetate, first 4:1 then 1:1) resulting in the isolation of 1.74 g (46% yield, 8.22 mmol) of the title compound.

Provenance & Evidence