Hydrochloric Acid → HCID 21940186, compound

Participants

Reaction Steps

To a solution having ethanol (34 mg, 0.74 mmol), triphenyl phosphine (204 mg, 0.78 mmol) and 5-(3-acetoxyphenyl)-4-(13-carboxy-1,1-dimethyl-3-oxatridecan-1-yl)-3,3-dimethyl-2,3-dihydrofuran (compound (22)) (126 mg, 0.258 mmol) dissolved in anhydrous THF (1.0 mL) in a nitrogen stream at room temperature and stirred, diethyl azodicarboxylate (135 mg, 0.77 mmol) dissolved in anhydrous THF (0.5 mL), was added, followed by stirring for 20 minutes. After completion of the reaction, the reaction mixture was put into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was put into a silica gel column and developed with a mixed solvent of hexane and ethyl acetate (20:1 to 10:1), whereby 5-(3-acetoxyphenyl)-4-(13-ethoxycarbonyl-1,1-dimethyl-3-oxatridecan-1-yl)-3,3-dimethyl-2,3-dihydrofuran (compound (24)) was obtained as a colorless oil in an amount of 111 mg in a yield of 83.3%.

Provenance & Evidence