Ethyl Acetate → HCID 19013937, compound

Participants

Reaction Steps

1.88 g (10 retool) of the crude (2R,3S)-2-methyl-3-tetrahydropyranyloxy-l-butanol was dissolved in 30 ml of DMF. Thereto was added 18.4 g of n-BuI. Thereto was further added carefully by small portions 4 g of oily sodium hydride (about 60%), with ice cooling. To the reaction mixture was added 300 ml of ethyl acetate. The insoluble materials were removed by filtration. The filtrate was washed with two 100 ml-portions of water, dried and concentrated under reduced pressure to obtain crude 1-butoxy-2-methyl-3-tetrahydropyranyloxybutane as an oily material. This crude product was dissolved in 150 ml of methanol. 5 g of Amberlist 15 was added thereto, and the mixture was stirred for 2 days at room temperature. The Amberlist 15 was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was subjected to Kugelrohr distillation to obtain 0.90 g of the title compound as an oily material.

Provenance & Evidence