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

HRID 1414989

反応式

HRID 1414989 の反応式
[CH2:1]([C@:3]12[CH2:11][CH2:10][C: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:8]=3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].N.[Li].[Cl-].[NH4+]>NC1C=CC=CC=1.O1CCCC1>[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]

参加物

7

反応物 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 11130013-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-olHCID 3028194Lithium

生成物 1

HCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol収率 82.8%

試薬・触媒・溶媒 2

HCID 6115Aniline溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 13β-ethyl-3-methoxy-gona-1,3,5(10), 8-tetraen-17β-ol (16.8 g.) dissolved in a mixture of aniline (150 cc.) and tetrahydrofuran (50 cc.) add liquid ammonia (400 cc.). Add lithium metal (6.0 g.) gradually in small pieces during 10 minutes, and stir the blue suspension obtained. After 2 hours, add ammonium chloride (50 g.) to the reaction mixture until a clear solution is obtained; then add water (600 cc.) and ether-extract the mixture. Evaporate the washed and dried extracts to obtain as residue a crystalline solid. Recrystallize from hexane (300 cc.), to obtain 13β-ethyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (14 g.), m.p. 126°-30°.

後処理

  1. customobtained
  2. customis obtained
  3. extractionthen add water (600 cc.) and ether-extract the mixture
  4. customEvaporate the
  5. washwashed
  6. customdried extracts
  7. customto obtain as residue a crystalline solid
  8. customRecrystallize from hexane (300 cc.)

出典と根拠

ORDレコード
ord-de588a2c72874406a9a3784526868512
出典データセット
uspto-grants-1977_01
特許番号
US04002746

関連ノート

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