Iodoethane → 17beta-Ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

HRID 1077243

반응식

HRID 1077243 반응식
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][CH3:21])=[CH:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].[H-].[Na+].[CH2:25](I)[CH3:26]>C1(C)C(C)=CC=CC=1>[CH2:25]([O:22][C@@H:4]1[C@:3]2([CH2:1][CH3:2])[C@H:7]([C@@H:8]3[CH2:19][CH2:18][C:17]4[CH:16]=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][C:12]=4[C@H:9]3[CH2:10][CH2:11]2)[CH2:6][CH2:5]1)[CH3:26]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

생성물 1

HCID 6814505317beta-Ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

Reflux a suspension of 5.0 g. of dl-13-ethyl-3-methoxygona-1,3,5(10)-trien-17β-ol and 3.83 g. of sodium hydride (50% in oil) for 1.5 hours in xylene (100 ml). Add 14.5 ml. of ethyl iodide and reflux for 22 hours. Acidify with 2N hydrochloric acid and extract the material with benzene. Chromatograph the residue on alumina (Grade I neutral). Elute the product with benzene-ether (1:1). Recrystallize the product from 60 ml. of methanol to obtain dl-17β-ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene (2.3 g); m.p. 74°-77°C.

후처리

  1. temperatureReflux
  2. additiona suspension of 5.0 g
  3. additionAdd 14.5 ml
  4. extractionAcidify with 2N hydrochloric acid and extract the material with benzene
  5. washElute the product with benzene-ether (1:1)
  6. customRecrystallize the product from 60 ml

출처 및 근거

ORD 기록
ord-f359b443dc924138aa60024011ef5eb7
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

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