Ethyl Acetate → HCID 57169364, compound

Participants

Reaction Steps

In 40 ml of N,N-dimethylformamide were dissolved 5.0 g of the (2S,3S)-2-methyl-3-(2-tetrahydropyranyloxy)butanol obtained in Example 1 i) and 24.5 g of butyl iodide. Thereto was added 1.22 g of oily sodium hydride (about 60%) in small portions with ice-cooling. The mixture was stirred for 2 hours with ice-cooling. The reaction mixture was poured into 300 ml of ethyl acetate and the resulting mixture was stirred. The insoluble materials were removed by filtration. The filtrate was washed with water three times. The organic layer was dried and concentrated. The residue, i.e. crude (2S,3S)-4-butoxy-3-methyl-2-(2-tetrahydropyranyloxy)butane was dissolved in 150 ml of methanol. To the solution was added 6.0 g of a nonaqueous strongly acidic cation exchange resin (Amberlist 15), and the mixture was stirred for 6 hours at room temperature. The cation exchange resin used was removed by filtration and the filtrate was concentrated. The residue was subjected to Kugelrohr distillation under reduced pressure to obtain 2.54 g of (2S, 3S )-4-butoxy-3-methyl-2-butanol.

Provenance & Evidence