Hydrochloric Acid → HCID 10954342, compound

Temperature

5 °C

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).

1. stirringthe mixture was stirred at the same temeprature for 40 minutes
2. extractionThen, the mixture was extracted with ethyl ether
3. washThe extract ether solution was washed with a 5% sodium bicarbonate aqueous solution
4. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled off from the ether layer
6. distillationAfter distilling off the solvent
7. customthe residue was purified by silica gel column chromatography
8. customto obtain 20.69 g (yield: 89%) of the

ORD record

ord-aff68acfc1604aa6bab7ab3715850aa6

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04985571