Ethyl Acetate → HCID 86758771, compound

Participants

Reaction Conditions

Reaction Steps

The compound (6) (176 mg, 130 μmol) was dissolved in dichloromethane (3 ml), followed by cooling to 0° C. Tetrabutylammonium fluoride (TBAF, 188 μl) was added and the mixture was stirred at room temperature for 24 hours. After confirming the completion of the reaction using TLC (AcOEt/Hex=1/2), the reaction mixture was concentrated under reduced pressure and the residue was dissolved in methanol (5 ml). A catalytic amount of sodium methoxide was added and the mixture was stirred at 40° C. for 24 hours. Further, water was added, followed by stirring for 24 hours. After confirming the completion of the reaction using TLC (CHCl3/MeOH/H2O=5/4/1), the reaction mixture was neutralized with an ion-exchange resin Amberlite IR-120 (H+), followed by removing the resin by filtration. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting syrup was purified by gel filtration (Sephadex LH-20, CHCl3/MeOH/H2O=5/4/0.7) to give a compound (1a) (78 mg, 90%).

Provenance & Evidence