反応 #81464

反応方程式

17-(3-Pyridyl)-5α-androst-16-en-3α-ol

aluminium isopropoxide

→

title compound

収率 86.0%

17-(3-Pyridyl)-5α-androst-16-en-3-one

収率 86.0%

溶媒

toluene

cyclohexanone

diethyl ether

反応条件

後処理

1. 1
   温度the mixture heated
2. 2
   温度under reflux for 90 min.
3. 3
   温度to cool
4. 4
   洗浄washed with aqueous trisodium citrate (15% w/v; 2×30 ml)
5. 5
   乾燥dried (Na2CO3)
6. 6
   濃縮concentrated
7. 7
   洗浄Chromatography, on elution with toluene-methanol (40:1)

実験手順

From a solution of 17-(3-Pyridyl)-5α-androst-16-en-3α-ol (1.05g, 3.0 mmol) in dry toluene (60 ml) and cyclohexanone (10 ml) was distilled off part of the solvent (20 ml) to eliminate moisture. After allowing to cool to 90° C., aluminium isopropoxide (1.02 g, 5.0 mmol) was added and the mixture heated under reflux for 90 min. then allowed to cool. The mixture was diluted with diethyl ether (250 ml), washed with aqueous trisodium citrate (15% w/v; 2×30 ml), dried (Na2CO3), and concentrated. Chromatography, on elution with toluene-methanol (40:1), afforded the title compound (0.90 g, 86%) which crystallised from toluene, m.p. 190°-192° C. IR νmax 1713 cm- ; 1H-NMR (CDCl3) inter alia δ 1.04 (3H,s,19-CH3), 1.07 (3H,s, 18-CH3), 5.98 (1M,16-H), 7.22 (1H,m,Py 5-H), 7.64 (1H,m,Py 4-H), 8.46 (1 H,m,Py 6-H), 8.61 (1H,m,Py 2-H); MS m/z 349 (M+). Anal. Calcd: C,82.47; H,8.94; N,4.01. Found: C.82.00; H,8.94; N,3.84%

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