Hydrochloric Acid → HCID 66937909, compound

Participants

Reaction Conditions

Reaction Steps

To an anhydrous THF (130 ml) solution of (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(2S,4R,5S)-4-methyl-2-phenyl-5-vinyl-1,3-dioxolan-4-yl] pentanoic acid (6.50 g, 15.5 mmol) was added triethylamine (2.80 ml, 20.2 mmol) under nitrogen atmosphere and cooled to 0° C. 2,4,6-Trichlorobenzoyl chloride (2.65 ml, 17.0 mmol) was added to the reaction solution. After the reaction solution was stirred at 0° C. for 10 minutes, it was stirred at room temperature for two hours. After the reaction solution was filtered with celite, the organic layer was concentrated under reduced pressure. To the obtained residue, an anhydrous toluene (130 ml) solution of (3S,4S,5E)-7-[(4-methoxybenzyl)oxy]-3,5-dimethylhepta-1,5-dien-4-ol (4.71 g, 17.0 mmol) and 4-dimethylaminopyridine (2.46 g, 20.2 mmol) were added under nitrogen atmosphere. After the reaction solution was stirred at room temperature for two hours, it was poured into 0.5N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution, water and brine sequentially, it was dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=10:1→5:1) to obtain the title compound (9.81 g) as a colorless oil.

Provenance & Evidence