Chloranil → Estra-4,6-diene-3,17-dione

HRID 352311

반응식

HRID 352311 반응식
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][C:12](=[O:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20].C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.CCOC(C)=O.CCCCCC>C(O)C>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][C:12](=[O:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20]

참가 물질

5

반응물 3

HCID 8371ChloranilHCID 92834(+)-Estr-4-ene-3,17-dioneHCID 21226206Ethyl acetate hexane

생성물 1

HCID 128845Estra-4,6-diene-3,17-dione수율 46.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of dione 53 (5.0 g, 18.36 mmol) and chloranil (5.4 g, 22 mmol) in dry ethanol (500 mL) was stirred at 60-65° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was triturated with dichloromethane. The solid was removed by filtration, and the filtrate was concentrated to give a brown gum. Chromatography (20% EtOAc/hexane) yielded crude dione 54 as a yellow solid (2.3 g, 46%): 1H NMR (300 MHz, CDCl3) δ0.94 (s, 3, CH3), 5.78 (s, 1), 6.25 (m, 2).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with dichloromethane
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customto give a brown gum

출처 및 근거

ORD 기록
ord-259aedf4be0f410e885a30194924abf9
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747018B2

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