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Diethyl Ether → 17-Hydroxy-3-methoxy-14,15-methylen-estra-1,3,5(a)-trien

HRID 224239
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HRID 224239 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C:12](=[O:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.CCOCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C@@H:12]([OH:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1.[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@:9]45[CH2:22][C@H:10]4[CH2:11][C@H:12]([OH:21])[C@:13]5([CH2:15][CH2:16]3)[CH3:14])[CH2:7][CH2:6][C:5]=2[CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 11130234HCID 11130234, 화합물HCID 21226445Aluminium lithium hydride

생성물 2

HCID 17323317-Hydroxy-3-methoxy-14,15-methylen-estra-1,3,5(a)-trienHCID 11022909HCID 11022909, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

100 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5-(10)-triene-17-one dissolved in 12 ml of absolute tetrahydrofuran are mixed with 100 mg of lithium aluminum hydride at 0° C. and set aside for 1.5 hours at room temperature. After adding ethyl acetate and ether the product is washed with saturated aqueous ammonium chloride solution and water, and the organic layer is separated, followed by drying with sodium sulphate and evaporating under vacuum. After preparative layer chromatography on silica gel (mobile phase: benzene/acetone/methanol 45:5:1) the residue yields 60 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5(10)-triene-17α-ol and 26 mg of 3-methoxy-14α,15α-methylene-estra-1,3,5(10)-triene-17β-ol.

후처리

  1. washis washed with saturated aqueous ammonium chloride solution and water
  2. customthe organic layer is separated
  3. dry with materialby drying with sodium sulphate
  4. customevaporating under vacuum

출처 및 근거

ORD 기록
ord-0ecc57ca3cf64724bb41d7d0a44a0390
출처 데이터셋
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04231946

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