Hydrochloric Acid → (2S,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadien-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of (1,1-dimethylethyl)[[(2S,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadienyl]oxy]dimethylsilane (6.74 g, 16.68 mmol) and THF (70 mL) is cooled to 0° C. 4 N aqueous HCl (70 mL) is added to the solution dropwise to maintain the reaction temperature at less than 5° C. The mixture is stirred at 0° C. for 1 h. The mixture is quenched by the addition of saturated aqueous NaCO3. The organic phase is separated. The aqueous phase is extracted with ethyl acetate (5×100 mL). The combined organic phase is washed with brine, dried over NaSO4 and concentrated. Flash chromatography gives the desired compound (4.17 g, 86%) as a clear oil.

Provenance & Evidence