Hydrochloric Acid → HCID 10954342, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 20.0 g (122 mmol) of (R)-O-benzylglycidol in dimethylsulfoxide (80 ml), 918.7 g (183 mmol) of a lithium acetylide-ethylenediamine complex (purity: 90%) was gradually added under stirring at a temperature of not higher than 5° C., and the mixture was stirred at the same temeprature for 40 minutes. To the reaction mixture, 150 ml of a saturated sodium chloride aqueous solution was added, and the mixture was acidified by an addition of concentrated hydrochloric acid. Then, the mixture was extracted with ethyl ether. The extract ether solution was washed with a 5% sodium bicarbonate aqueous solution and then with a saturated sodium chloride aqueous solution. The ether layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off from the ether layer. After distilling off the solvent, the residue was purified by silica gel column chromatography to obtain 20.69 g (yield: 89%) of the above identified terminal acetylene compound. Boiling point: 95° C. (0.3 Torr).

Provenance & Evidence