反応 #6150

反応方程式

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

収率 67.0%

溶媒

ether

THF

THF

反応条件

後処理

1. 1
   その他remained below -70° C
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   その他the solvent was evaporated off
4. 4
   抽出The reaction mixture remaining behind was extracted with ether
5. 5
   その他the ethereal phase was dried
6. 6
   その他evaporated

実験手順

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.

出典