Aluminum isopropoxide → 3-Hydroxy-2-iodo-estra-1,3,5(10)-triene-7,17-dione

HRID 28342

반응식

HRID 28342 반응식
[OH:1][C:2]1[C:19]([I:20])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:21])[CH2:10][CH2:9]4)[C@@H:6]([OH:22])[CH2:5][C:4]=2[CH:3]=1.CC([O-])C.CC([O-])C.CC([O-])C.[Al+3]>C1(C)C=CC=CC=1.C1(=O)CCCCC1>[OH:1][C:2]1[C:19]([I:20])=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:21])[CH2:10][CH2:9]4)[C:6](=[O:22])[CH2:5][C:4]=2[CH:3]=1

참가 물질

5

반응물 2

HCID 11143Aluminum isopropoxideHCID 116112933,7beta-Dihydroxy-2-iodo-estra-1,3,5(10)-trien-17-one

생성물 1

HCID 116829833-Hydroxy-2-iodo-estra-1,3,5(10)-triene-7,17-dione수율 63%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 7967Cyclohexanone용매

실험 절차

A solution of 206 mg (0.5 mmol) of 3,7β-dihydroxy-2-iodo-estra-1,3,5(10)-trien-17-one 14 in 15 ml of toluene and 4 ml of cyclohexanone was heated to 140° C. (oil bath temperature), and a solution of 400 mg of aluminum isopropylate in 10 ml of toluene was added drop by drop. In the meantime, a portion of the reaction mixture was distilled off. After complete addition of the aluminum isopropylate, it was refluxed for still another 5 hours. Then, the reaction solution was cooled and diluted with 80 ml of dichloromethane and 30 ml of potassium/sodium tartrate solution, and the resulting mixture was first stirred vigorously for 30 minutes before the organic phase was separated from the aqueous phase. The aqueous phase was finally extracted with dichloromethane (3×30 ml), and the combined organic phases were washed with a saturated NaCl solution, dried on sodium sulfate and concentrated by evaporation in a rotary evaporator. Flash chromatography (cyclohexane/ethyl acetate) yielded 129 mg (63%) of colorless crystals.

후처리

  1. distillationIn the meantime, a portion of the reaction mixture was distilled off
  2. additionAfter complete addition of the aluminum isopropylate, it
  3. temperaturewas refluxed for still another 5 hours
  4. temperatureThen, the reaction solution was cooled
  5. additiondiluted with 80 ml of dichloromethane and 30 ml of potassium/sodium tartrate solution
  6. customwas separated from the aqueous phase
  7. extractionThe aqueous phase was finally extracted with dichloromethane (3×30 ml)
  8. washthe combined organic phases were washed with a saturated NaCl solution
  9. customdried on sodium sulfate
  10. concentrationconcentrated by evaporation in a rotary evaporator

출처 및 근거

ORD 기록
ord-ba0076bd14184a21bb44fc4c93e651f8
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419972B2

연결된 노트

불러오는 중…