Reaktion #214062

Reaktionsgleichung

1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chloro-butan-2-one naphthalene-1,5-disulphonate

sodium bicarbonate

sodium borohydride

→

1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chloro-butan-2-ol

Ausbeute 75.0%

Lösungsmittel

methylene chloride

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase was separated off
2. 2
   Trocknendried over sodium sulphate
3. 3
   Einengenconcentrated
4. 4
   workup.DISTILLATIONby distilling off the solvent in vacuo
5. 5
   SonstigeThe base thus obtained
6. 6
   workup.DISTILLATIONthe isopropanol was then distilled off
7. 7
   workup.ADDITIONafter adding 100 ml of water
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature for a further 15 hours
9. 9
   SonstigeThe organic phase was then separated off
10. 10
    Waschenwashed twice with 50 ml of water each time
11. 11
    Trocknendried over sodium sulphate
12. 12
    Einengenconcentrated
13. 13
    SonstigeThe oil which remained was boiled up in 100 ml of petroleum ether, whereupon crystallization

Vorschrift

18.8 g (0.04 mol) of 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chloro-butan-2-one naphthalene-1,5-disulphonate were suspended in 100 ml of methylene chloride, and 100 ml of sodium bicarbonate solution were added. The organic phase was separated off, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The base thus obtained was taken up in 100 ml of isopropanol, and 2 g (0.05 mol) of sodium borohydride were added in portions at 5° to 10° C. The mixture was stirred at room temperature for 15 hours and the isopropanol was then distilled off. The residue was taken up in 100 ml of methylene chloride and, after adding 100 ml of water, the mixture was stirred at room temperature for a further 15 hours. The organic phase was then separated off, washed twice with 50 ml of water each time, dried over sodium sulphate and concentrated. The oil which remained was boiled up in 100 ml of petroleum ether, whereupon crystallization occurred. 9.8 g (75% of theory) of 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chloro-butan-2-ol of melting point 120°-125° C. were obtained. ##STR15##

Quelle