Reaktion #1848031

Reaktionsgleichung

3-hydroxy-4-methylestra-1,3,5(10)-trien-17-one

1-adamantanol

boron trifluoride diethyl etherate

→

pure product

Ausbeute 68.0%

2-(1-admantanyl)-3-hydroxy-4-methylestra-1,3,5(10)-trien-17-one

Ausbeute 68.0%

Lösungsmittel

pentane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooling with an ice bath
2. 2
   workup.STIRRINGAfter stirring at 0° C. for 15 min. the reaction
3. 3
   workup.STIRRINGwas stirred at room temperature for 45 min
4. 4
   workup.ADDITIONIce was added
5. 5
   Sonstigethe white solid that formed
6. 6
   Filtrationwas filtered
7. 7
   Waschenwashed with water
8. 8
   Trocknendried over P2O5
9. 9
   SonstigeThe crude product was purified by chromatography (silica gel eluted with 7% ethyl acetate in hexanes)

Vorschrift

To a suspension of the known 3-hydroxy-4-methylestra-1,3,5(10)-trien-17-one (ref. Kaneko et al., 1964; Chemical Abstracts Registry Number [68969-90-4], 30 mg, 0.11 mmol) and 30 mg (0.197 mmol) of 1-adamantanol in 1 mL of anhydrous pentane was added 0.02 mL of boron trifluoride diethyl etherate while cooling with an ice bath and stirring. After stirring at 0° C. for 15 min. the reaction was stirred at room temperature for 45 min. Ice was added and the white solid that formed was filtered, washed with water and dried over P2O5. The crude product was purified by chromatography (silica gel eluted with 7% ethyl acetate in hexanes) to give 30 mg of pure product (68% yield). After recrystallization from methylene chloride-hexanes the product had: m.p. 262-263° C.; 1H NMR(CDCl3) δ 0.90 (s, 3H, CH3), 2.13 (s, 3H, CH3), 2.7 (m, 2H, CH2), 7.11 (s, 1H, Ar—H); 13C NMR (CDCl3) δ 11.02, 13.70, 21.44, 26.22, 26.67, 27.54, 28.95 (3×C), 31.56, 35.84, 36.60, 36.98 (3×C), 37.63, 40.82 (3×C), 44.60, 47.91, 50.34, 121.41, 121.51, 131.45, 133.32, 150.79, 221.49. (Anal. calc'd. for C29H39O2: C, 83.21; H, 9.15. Found: C, 83.45; H, 8.94.)

Quelle