Sodium Bicarbonate → ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate

Participants

Reaction Conditions

Reaction Steps

Concentrated hydrochloric acid (10 drops) was added to a solution of ethyl 10-[(3RS,4RS)-7-(methoxymethoxy)-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate (1.33 g, 1.686 mmol) in methanol (15 ml) followed by stirring for 4 hours at 50° C. The reaction mixture was neutralized with aqueous sodium bicarbonate and then concentrated under reduced pressure. Water was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4) to give ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate (1.10 g, Yield 93%) as a colorless oil.

Provenance & Evidence