Aluminum isopropoxide → 3-Methoxyestra-2,5(10)-dien-17-one

HRID 1415057

반응식

HRID 1415057 반응식
[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(=O)CCCCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]1=[O:21]

참가 물질

5

반응물 2

HCID 11143Aluminum isopropoxideHCID 1019633-Methoxyestra-2,5(10)-dien-17beta-ol

생성물 1

HCID 227914253-Methoxyestra-2,5(10)-dien-17-one수율 88.1%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 7967Cyclohexanone용매

실험 절차

Dissolve dl-3-methoxyestra-2,5(10)-dien-17β-ol (4 g) in cyclohexanone (40 ml) and toluene (140 ml) and add a solution of aluminum isopropoxide (4 g) in toluene (56 ml). Reflux in an atmosphere of nitrogen for two hours and cool. Add water (7.5 ml), shake, and then dry by adding sodium sulfate (10 g). Filter and evaporate under vacuum and recrystallize the residue from methanol to obtain dl-3-methoxyestra-2,5(10)-dien-17-one (3.5 g); m.p. 116°-118°; infrared absorption maxima at 5.76 μ, 5.9 μ, 6.01 μ.

후처리

  1. temperatureReflux in an atmosphere of nitrogen for two hours
  2. temperaturecool
  3. dry with materialAdd water (7.5 ml), shake, and then dry
  4. additionby adding sodium sulfate (10 g)
  5. filtrationFilter
  6. customevaporate under vacuum
  7. customrecrystallize the residue from methanol

출처 및 근거

ORD 기록
ord-c5457bcecc1a44e6872f38b3d07e5aa6
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04002746

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