Reaktion #51638

Reaktionsgleichung

toluenesulfonic acid monohydrate

2-Methoxyestra-1,3,5(10),15-tetraen-3-ol-17-one

isopropenyl acetate

acetic anhydride

→

diacetate

Ausbeute 80.8%

2-Methoxy-3,17-diacetoxyestra-1,3,5(10),14,16-pentaene

Ausbeute 80.8%

Lösungsmittel

CH2Cl2

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturto reflux for 6 h
3. 3
   Sonstigea complete reaction
4. 4
   ExtraktionThe mixture was extracted with methylene chloride (3×)
5. 5
   WaschenThe organic fractions were washed with water (1×), saturated sodium bicarbonate solution (1×) and water (1×)
6. 6
   Filtrationfiltered through anhydrous sodium sulfate
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was crystallized from methanol

Vorschrift

Under nitrogen, toluenesulfonic acid monohydrate (0.1 g, 0.53 mmol) was added to a solution of 2-Methoxyestra-1,3,5(10),15-tetraen-3-ol-17-one prepared in Example 3 (0.25 g, 0.84 mmol), isopropenyl acetate (5 mL, 45.15 mmol) and acetic anhydride (5 mL, 53 mmol) and the mixture was heated to reflux for 6 h. At the end of that time, analysis by tlc (2% acetone in CH2Cl2) indicated a complete reaction. The reaction was cooled to room temperature, poured into ice water (˜100 mL) and stirred for 1 h. The mixture was extracted with methylene chloride (3×). The organic fractions were washed with water (1×), saturated sodium bicarbonate solution (1×) and water (1×), filtered through anhydrous sodium sulfate, combined and concentrated in vacuo. The residue was crystallized from methanol to give the pure diacetate (17) (0.259 g, 80.8%).

Quelle