p-Toluenesulfonic acid → (13S)-Ethyl-3-methoxygona-1,3,5(10),16-tetraen-17-ol Acetate

反応式

[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:8]([C@H:9]4[C@@:13]([CH2:16][CH2:17]3)([CH2:14][CH3:15])[C:12](=[O:22])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([CH2:37][C:38]([O-])=[O:39])(C)=C>C(OCC)(=O)C>[C:38]([O:22][C:12]1[C@:13]2([CH2:16][CH2:17][C@H:18]3[C@@H:8]([CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:21]=[CH:20][C:19]=43)[C@@H:9]2[CH2:10][CH:11]=1)[CH2:14][CH3:15])(=[O:39])[CH3:37]

参加物

実験手順

30 g of 3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one [J. Org. Chem. 40 (1975) 681] is stirred for 22 hours at 120° C. in 200 ml of isopropenylacetate with 1.5 g of p-toluenesulfonic acid. It is then diluted with ethyl acetate, washed with sodium carbonate and a common salt (NaCl) solution, dried over sodium sulfate and concentrated. After chromatography, 27.6 g of 17-acetoxy-3-methoxy-18-methyl-1,3,5(10),16-estratetraene with a melting point of 105°-106° C. is obtained.