反応 #56620

反応方程式

3,7β-dihydroxy-2-iodo-estra-1,3,5(10)-trien-17-one

aluminum isopropylate

→

colorless crystals

収率 63.0%

3-Hydroxy-2-iodo-estra-1,3,5(10)-triene-7,17-dione

収率 63.0%

溶媒

toluene

cyclohexanone

toluene

反応条件

後処理

1. 1
   workup.DISTILLATIONIn the meantime, a portion of the reaction mixture was distilled off
2. 2
   workup.ADDITIONAfter complete addition of the aluminum isopropylate, it
3. 3
   温度was refluxed for still another 5 hours
4. 4
   温度Then, the reaction solution was cooled
5. 5
   workup.ADDITIONdiluted with 80 ml of dichloromethane and 30 ml of potassium/sodium tartrate solution
6. 6
   その他was separated from the aqueous phase
7. 7
   抽出The aqueous phase was finally extracted with dichloromethane (3×30 ml)
8. 8
   洗浄the combined organic phases were washed with a saturated NaCl solution
9. 9
   その他dried on sodium sulfate
10. 10
    濃縮concentrated by evaporation in a rotary evaporator

実験手順

A solution of 206 mg (0.5 mmol) of 3,7β-dihydroxy-2-iodo-estra-1,3,5(10)-trien-17-one 14 in 15 ml of toluene and 4 ml of cyclohexanone was heated to 140° C. (oil bath temperature), and a solution of 400 mg of aluminum isopropylate in 10 ml of toluene was added drop by drop. In the meantime, a portion of the reaction mixture was distilled off. After complete addition of the aluminum isopropylate, it was refluxed for still another 5 hours. Then, the reaction solution was cooled and diluted with 80 ml of dichloromethane and 30 ml of potassium/sodium tartrate solution, and the resulting mixture was first stirred vigorously for 30 minutes before the organic phase was separated from the aqueous phase. The aqueous phase was finally extracted with dichloromethane (3×30 ml), and the combined organic phases were washed with a saturated NaCl solution, dried on sodium sulfate and concentrated by evaporation in a rotary evaporator. Flash chromatography (cyclohexane/ethyl acetate) yielded 129 mg (63%) of colorless crystals.

出典