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

HRID 1077171

반응식

HRID 1077171 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. Evaporated 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. customEvaporated 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-8cb3876bc98147049953cd80e083c32f
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

연결된 노트

불러오는 중…