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

HRID 371810

반응식

HRID 371810 반응식
[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

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 25237919-Hydroxyandrostenedione

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dd803cd3723f47a39891acfd9ac3d996
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04087524

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