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

HRID 1077243

反応式

HRID 1077243 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f359b443dc924138aa60024011ef5eb7
出典データセット
uspto-grants-1976_05
特許番号
US03959322

関連ノート

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