Sodium Carbonate → 19-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-one

HRID 597357

반응식

HRID 597357 반응식
[O:1]=[C:2]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][O:22]C(=O)CC)[C:15](=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)[CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:22][CH2:21][C@@:20]12[C@@H:27]3[C@H:12]([C@H:9]4[C@@:7]([CH2:29][CH2:28]3)([CH3:8])[C@@H:6]([O:5][C:2](=[O:1])[CH2:3][CH3:4])[CH2:11][CH2:10]4)[CH2:13][CH2:14][C:15]1=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]2

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 5434261217beta,19-Bis(1-oxopropoxy)-androst-4-en-3-one

생성물 1

HCID 5422328719-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

A solution of 11 g of 17β,19-bis(1-oxopropoxy)androst-4-en-3-one in 2 liters of methanol is treated with 2.5 g of sodium carbonate in 250 ml of water and refluxed for one hour after which the reaction mixture is poured into 10 liters of water, and the solid collected by filtration. The solid is dissolved in methylene chloride, dried over magnesium sulfate, filtered and the solvent removed. The residue is crystallized from acetone-hexane yielding 6 g of 19-hydroxy-17β(1-oxopropoxy)androst-4-en-3-one. M.P. 160°-162° C.

후처리

  1. temperaturerefluxed for one hour after which the reaction mixture
  2. filtrationthe solid collected by filtration
  3. dissolutionThe solid is dissolved in methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe residue is crystallized from acetone-hexane yielding 6 g of 19-hydroxy-17β(1-oxopropoxy)androst-4-en-3-one

출처 및 근거

ORD 기록
ord-a7ea5910cdac4fe9a60d62136b886b9d
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04013762

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