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

HRID 1414989

반응식

HRID 1414989 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6115Aniline용매HCID 8028Tetrahydrofuran용매

실험 절차

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°.

후처리

  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.)

출처 및 근거

ORD 기록
ord-de588a2c72874406a9a3784526868512
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04002746

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