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Sodium Bicarbonate → (17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

HRID 918544
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HRID 918544 반응식
C([O:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C@H:11]3[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C@H:11]3[CH2:12][CH2:13]2)[CH2:8][CH2:7]1
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반응물 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 18595372(+)-17beta-Tert.butoxy-13 beta-ethyl-3-methoxygona-1,3,5(10)-triene

생성물 1

HCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol수율 103.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 0.4 g (1.12 mmoles) of (+)-17β-tert.butoxy-13 β-ethyl-3-methoxygona-1,3,5(10)-triene and 0.1 g of p-toluenesulfonic acid monohydrate in 10 ml of toluene was stirred and heated at reflux for 1 hr. The resulting solution was cooled and treated with saturated aqueous sodium bicarbonate solution then extracted twice with ether. The combined organic extracts were dried, filtered and concentrated in vacuo giving 0.348 g of (+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene as a colorless solid.

후처리

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. temperatureThe resulting solution was cooled
  4. extractionthen extracted twice with ether
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e68b4df0771a4eca8c89b8a157f3a9db
출처 데이터셋
uspto-grants-1976_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03971809

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