Methyl Acetate → Methyl 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-3-hydroxypentanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.5 g of diisopropylamine in 25 ml of tetrahydrofuran (THF), stirred at -78° C. in an atmosphere of nitrogen, was added 6.5 ml of 1.6M n-butyllithium in hexane. The mixture was stirred at -78° C. for 5 min after which a solution of 1.2 g of methyl acetate in 5 ml of THF was added. The mixture was again stirred at -78° C. for 5 min. Then a solution of 1.75 g of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal, the product of Example 3, in 20 ml of THF was added. The reaction mixture was stirred at -78° C. for 1/2 hr. A saturated solution of ammonium chloride was carefully added, and the resultant mixture was allowed to warm to room temperature. The mixture was extracted with ether. The ether extract was washed with water, dried over anydrous MgSO4, and distilled to dryness under reduced pressure. The residual oil was chromatographed on silica gel. Elution with hexane-ethyl acetate followed by crystallization from aqueous methanol gave the product mp. 77°-80° C.

Provenance & Evidence