Reacción #65913

Ecuación de reacción

title product

(cis)-2-[2-[3,5-bis(1,1-dimethylethyl)phenyl]-ethyl]cyclopentyl-4-methylbenzenesulfonate

sodium methoxide

methyl thioglycolate

→

title compound

methyl(trans)-2-[[2-[2-[3,5-bis(1,1-dimethylethyl) -phenyl]ethyl]cyclopentyl]thio]acetate

Disolventes

methanol

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   OtroThe mixture is then partitioned between diethyl ether and water
3. 3
   Secadothe organic layer dried over sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated

Procedimiento

To a solution of sodium methoxide (prepared from 38 mg of sodium) in 10 ml of methanol is added 174 mg (1.64 mmoles) of methyl thioglycolate. After stirring for a few minutes, a solution of 500 mg (1.09 mmoles) of the title product of Example 38 in 5 ml of methanol is added, and stirring is continued until TLC indicates the reaction is complete. The mixture is then partitioned between diethyl ether and water, the organic layer dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane as eluents gives the title compound.

Fuente