Reacción #6150

Ecuación de reacción

hydrochloric acid

t-butyl [(S)-p-tolylsulfinyl]acetate

t-butylmagnesium bromide

(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-tetradecanal

→

t-butyl 3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2-[(S)-p-tolylsulfinyl]-hexadecanoate

Rendimiento 67.0%

Disolventes

ether

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroremained below -70° C
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   Otrothe solvent was evaporated off
4. 4
   ExtracciónThe reaction mixture remaining behind was extracted with ether
5. 5
   Otrothe ethereal phase was dried
6. 6
   Otroevaporated

Procedimiento

G)a) 16.5 g of t-butyl [(S)-p-tolylsulfinyl]acetate were dissolved in a mixture of 600 ml of ether and 60 ml of THF and cooled to -78° C. 43 ml of t-butylmagnesium bromide were then added dropwise in such a manner that the temperature remained below -70° C. After stirring at -78° C. for 1 hour 13.4 g of (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-tetradecanal in 100 ml of THF were added dropwise. After 2 hours at -78° C. the reaction mixture was hydrolyzed with 2N hydrochloric acid and the solvent was evaporated off. The reaction mixture remaining behind was extracted with ether and the ethereal phase was dried and evaporated. After chromatography on silica gel there were obtained 14.9 g of t-butyl 3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2-[(S)-p-tolylsulfinyl]-hexadecanoate (67% yield). m.p. 97°-98° C.

Fuente