Reaktion #44600

Reaktionsgleichung

sodium sulfite

1,2,3-Trifluoro-5-((E)-propenyl)benzene

AD-Mix-α

methanesulfonamide

water

→

title compound

(1S,2S)-1-(3,4,5-trifluorophenyl)propane-1,2-diol

Lösungsmittel

tert-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 1 hr
3. 3
   ExtraktionThe reaction solution was extracted with methylene chloride three times
4. 4
   Waschenwashed with a 2 N sodium hydroxide aqueous solution
5. 5
   ExtraktionThe sodium hydroxide layer was re-extracted with methylene chloride
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

Vorschrift

1,2,3-Trifluoro-5-((E)-propenyl)benzene (5.83 g) was added to a solution mixture of tert-butanol (170 mL) and water (170 mL) of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g) under ice-cooling. This reaction solution was stirred at 5° C. overnight. Then, sodium sulfite (51 g) was added to the reaction solution, and the resulting mixture was stirred at room temperature for 1 hr. The reaction solution was extracted with methylene chloride three times. All the organic layers were combined and washed with a 2 N sodium hydroxide aqueous solution. The sodium hydroxide layer was re-extracted with methylene chloride. All the organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to give 5.54 g of the title compound. The physical property values of this compound were as follows:

Quelle