1,2-Dimethoxyethane → Testosterone, acetate

HRID 1576165노트

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HRID 1576165 반응식
[CH3:1]P(=O)(OCCCC)OCCCC.C(COC)OC.C([Li])CCC.[C:25]([O:28][C@H:29]1[CH2:34][CH2:33][C@H:32]2[C@H:35]3[C@H:45]([CH2:46][CH2:47][C@:30]12[CH3:31])[C@:43]1([CH3:44])[C:38](O[C:40](=[O:48])[CH2:41][CH2:42]1)=[CH:37][CH2:36]3)(=[O:27])[CH3:26]>CCCCCC.O.O1CCCC1>[CH3:26][C:25]([O:28][C@@H:29]1[C@@:30]2([CH3:31])[CH2:47][CH2:46][C@@H:45]3[C@:43]4([CH3:44])[C:38](=[CH:1][C:40]([CH2:41][CH2:42]4)=[O:48])[CH2:37][CH2:36][C@H:35]3[C@@H:32]2[CH2:33][CH2:34]1)=[O:27]

참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 16994Dibutyl methylphosphonateHCID 5390371317beta-Acetoxy-4-oxa-androst-5-en-3-oneHCID 178418339Butyllithium

생성물 1

HCID 92145Testosterone, acetate

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a suspension of 4 g. of dibutyl methylphosphonate in 75 ml. of dry monoglyme at about -78° under nitrogen, there is added with stirring one equivalent of n-butyl lithium in hexane. After about 10 minutes, there is added one equivalent of 17β-acetoxy-4-oxa-androst-5-en-3-one in 75 ml. of dry tetrahydrofuran while maintaining the temperature at about -78°. The reaction mixture is allowed to warm to room temperature and then left to stand for about four hours. The reaction mixture is diluted with water and extracted with ether. The ether extracts are combined, washed, dried and evaporated to give testosterone acetate (17β-acetoxyandrost-4-en-3-one) which can be purified by chromatography.

후처리

  1. additionTo a suspension of 4 g
  2. waitleft
  3. waitto stand for about four hours
  4. extractionextracted with ether
  5. washwashed
  6. customdried
  7. customevaporated

출처 및 근거

ORD 기록
ord-e61a96219f5349b19110d81e6911fac4
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03979458

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