3-((benzyloxy)methyl)oxetane

Synthesis

117087-18-0

1003013-76-0

General procedure for the synthesis of 3-(benzyloxymethyl)oxetane from 2-((benzyloxy)methyl)propane-1,3-diol: the white powder (75 g, 0.38 mol) obtained in step (3) was dissolved in N,N-dimethylformamide (1 L), placed in an ice bath, and under partial protection of nitrogen, sodium hydride was added in batches (15.2 g, 0.38 mol. 60% dispersed in mineral oil). After stirring for 1 h, methanesulfonyl chloride (43 g, 0.375 mol) was added slowly and dropwise. The reaction system was gradually warmed to room temperature and stirring was continued for 2 hours. Subsequently, the system was cooled to 0 °C, sodium hydride (15.2 g, 0.38 mol) was added in batches, slowly warmed to room temperature and stirring was continued for 3 hours. The pH was adjusted to neutral with 1 M hydrochloric acid under ice bath conditions. Add 2 L of water and extract with ethyl acetate (300 mL each time, 5 times). The organic phases were combined, washed 3 times with water, dried and concentrated. The residue was dissolved in 500 mL of methanol. 100mL of petroleum ether was added to the methanol solution, stirred for 20 minutes and then layered. Repeatedly added 100mL of petroleum ether, stirred for 20 minutes, partitioned, and collected the lower layer to concentrate. Crystallization was carried out through a solvent mixture of ethyl acetate and petroleum ether (1:10) to give 53 g of white solid in 78% yield.

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