Reaktion #485796

Reaktionsgleichung

sodium borohydride

(E)-3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester

→

racemic 3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester

Ausbeute 97.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturto warm to 25° C. where it
3. 3
   workup.STIRRINGwas stirred for 15 h
4. 4
   FiltrationThe black solid was filtered
5. 5
   Filtrationusing filter paper
6. 6
   Waschenwashed with methanol
7. 7
   EinengenThe combined solvents were concentrated in vacuo
8. 8
   workup.ADDITIONthe residue was diluted with water (50 mL) and ethyl acetate (50 mL)
9. 9
   SonstigeThe two layers were separated
10. 10
    Extraktionthe aqueous layer was extracted with ethyl acetate (1×25 mL)
11. 11
    WaschenThe combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×50 mL)
12. 12
    Trocknendried over anhydrous magnesium sulfate
13. 13
    Filtrationfiltered
14. 14
    Einengenconcentrated in vacuo

Vorschrift

A solution of nickel(II) chloride hexahydrate (157 mg, 0.66 mmol) and (E)-3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester (1.07 g, 3.31 mmol) in methanol (30 mL) was cooled to 0° C. and then treated with sodium borohydride (380 mg, 10 mmol) in four portions. After the addition, the black reaction mixture was stirred for 15 min at 0° C. and then allowed to warm to 25° C. where it was stirred for 15 h. The black solid was filtered using filter paper and washed with methanol. The combined solvents were concentrated in vacuo, and the residue was diluted with water (50 mL) and ethyl acetate (50 mL). The two layers were separated, and the aqueous layer was extracted with ethyl acetate (1×25 mL). The combined organic extracts were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford racemic 3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester (1.04 g, 97%) as an amorphous white solid: EI-HRMS m/e calcd for C17H24O4S (M+) 324.1395, found 324.1395.

Quelle