反応 #44632

反応方程式

AD-Mix-α

methanesulfonamide

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

water

sodium sulfite

→

title compound

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

溶媒

tert-butanol

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他The resulting reaction solution
3. 3
   その他The resulting reaction solution
4. 4
   workup.STIRRINGwas stirred at room temperature for 1 hr
5. 5
   抽出extracted with methylene chloride three times
6. 6
   洗浄washed with a 2 N sodium hydroxide aqueous solution
7. 7
   抽出The sodium hydroxide layer was re-extracted with methylene chloride
8. 8
   乾燥dried over anhydrous magnesium sulfate
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The obtained crude product
11. 11
    その他was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

実験手順

To an ice-cooled solution mixture of tert-butanol (170 mL) and water (170 mL) of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g), 1,2,3-trifluoro-5-((E)-propenyl)benzene (5.83 g) was added. The resulting reaction solution was stirred at 5° C. overnight, and then sodium sulfite (51 g) was added thereto. The resulting reaction solution was stirred at room temperature for 1 hr, and then extracted with methylene chloride three times. 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. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude product 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:

出典