Methanol → HCID 19023769, compound

Participants

Reaction Steps

The compound of Example 1(c) (722 mg, 2 mmol) was dissolved in methanol (10 ml) containing 2% triethylamine and the solution was stirred under argon at room temperature. Triethylamine (1.68 ml, 12 mmol) and 4-hydroxythiophenol (428 mg, 3.4 mmol) were dissolved in methanol (15 ml) and added to the reaction mixture which was then stirred overnight at room temperature. The solvent was evaporated and the residue was flash chromatographed on 80 grams of silica gel eluted with 30% ethyl acetate/hexane to give a mixture of the desired product and its regioisomer, methyl 3-hydroxy-2-(4-hydroxyphenylthio)-3[2-(8-phenyloctyl)phenyl]propionate. The mixture of regioisomers was dissolved in methanol (20 ml) and stirred under argon at room temperature. Sodium methoxide, 25 wt. % in methanol, (0-92 ml, 4 mmol) was added dropwise and the mixture-stirred for 2.5 hours. The mixture was cooled in an ice bath and acetic acid (0.3 ml, 5.2 mmol) was added dropwise. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to give the crude product which was flash chromatographed on 80 grams of silica gel eluted with 25% ethyl acetate/hexane to give the desired product.

Provenance & Evidence