Pyridine → 19-Trimethylsiloxy-4-androstene-3,17-dione

HRID 371810

反応式

HRID 371810 の反応式
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.[CH3:23][Si:24]([CH3:27])([CH3:26])Cl.N1C=CC=CC=1>C1C=CC=CC=1>[CH3:23][Si:24]([CH3:27])([CH3:26])[O:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2

参加物

5

反応物 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 25237919-Hydroxyandrostenedione

生成物 1

HCID 2280149719-Trimethylsiloxy-4-androstene-3,17-dione

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 9.0 gm (0.03 mole) of 19-hydroxy-4-androstene-3,17-dione, 4.3 gm (0.04 mole) of trimethylchlorosilane and 3.2 gm (0.04 mole) of pyridine is refluxed in 100 ml of benzene for a period of 18 hours. The resulting suspension is filtered, the volatiles removed in vacuo and concentrated to a yellow oil. The oil is placed upon a silica gel chromatographic column packed in chloroform and eluted with chloroform. The chloroform eluate is evaporated to dryness in vacuo and the residue is recrystallized twice from hexane to yield the desired 19-(trimethylsiloxy)-4-androstene-3,17-dione having a m.p. of 87°-9° C., uv max (MeOH) 242 nm (ε14,700).

後処理

  1. filtrationThe resulting suspension is filtered
  2. customthe volatiles removed in vacuo
  3. concentrationconcentrated to a yellow oil
  4. washeluted with chloroform
  5. customThe chloroform eluate is evaporated to dryness in vacuo
  6. customthe residue is recrystallized twice from hexane

出典と根拠

ORDレコード
ord-dd803cd3723f47a39891acfd9ac3d996
出典データセット
uspto-grants-1978_05
特許番号
US04087524

関連ノート

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