Acetic Acid → 2-Methoxyestrone

HRID 1644248

반응식

HRID 1644248 반응식
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.II.[C:23](O)(=[O:25])C>[Cu](Cl)Cl>[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[C:11]([CH2:12][CH2:13]1)=[CH:10][C:9]([OH:20])=[C:8]([O:25][CH3:23])[CH:7]=3)[CH2:4][CH2:3]2

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 807IodineHCID 5870Estrone

생성물 1

HCID 4406242-Methoxyestrone수율 75%

시약·촉매·용매 1

HCID 24014Cupric Chloride촉매

실험 절차

To this end, 2-iodo-estrone 49 was prepared by treating oestrone with mercuric acetate and iodine in acetic acid.40 The selective halogenation at position 2 was complete within 2 hours at room temperature with an overall yield of 56% after successive recrystallizations. 2-Iodo-estrone then reacted with a large excess of a freshly prepared solution of sodium methoxyde, in presence of copper chloride in refluxing pyridine41 and gave 2-methoxy-estrone 50 with a yield of 75%. This method has the advantage of not involving any protecting group and gives good overall yield (42%) for the synthesis of 2-methoxy-estrone in two steps from oestrone.

후처리

  1. customafter successive recrystallizations
  2. custom2-Iodo-estrone then reacted with a large excess of a freshly prepared solution of sodium methoxyde

출처 및 근거

ORD 기록
ord-091038619cb044aca43e76640a22e516
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124614B2

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