Sodium Carbonate → Methyl 7-[5-((1E)(3S)-3-hydroxyoct-1-enyl)(1R,4R,5R)-4-hydroxy-2-oxocyclopentyl]heptanoate

Participants

Reaction Conditions

Reaction Steps

(−)-methyl(11R, 15S, 13E)-11-tert-butyldimethylsilyloxy-15-hydroxy-9-oxoprost-13-en-1-oate (481 mg, 1.0 mmol) was dissolved in 5 ml of a mixed solvent (ethyl acetate/water/tetrahydrofuran 6:3:1) and stirred at 40° C. for 2 h. The reaction mixture was poured into a saturated aqueous sodium carbonate cooled with ice and extracted with ethyl acetate (100 ml) two times. The combined organic layer was washed with a saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to remove solvent. The residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)] to give 312 mg (85% yield) of prostaglandin E1 methyl ester;

Provenance & Evidence