Decanoyl chloride → (8R,9S,10R,13S,14S,17S)-13-ethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl decanoate

HRID 1077192

반응식

HRID 1077192 반응식
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:13]([C@:15]12[CH2:23][CH2:22][C@@H:21]3[C@@H:24]4[C:29]([CH2:30][CH2:31][C@H:20]3[C@@H:19]1[CH2:18][CH2:17][C@@H:16]2[OH:33])=[CH:28][C:27](=[O:32])[CH2:26][CH2:25]4)[CH3:14]>N1C=CC=CC=1.Cl>[CH2:13]([C@:15]12[CH2:23][CH2:22][C@@H:21]3[C@@H:24]4[C:29]([CH2:30][CH2:31][C@H:20]3[C@@H:19]1[CH2:18][CH2:17][C@@H:16]2[O:33][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:28][C:27](=[O:32])[CH2:26][CH2:25]4)[CH3:14]

참가 물질

5

반응물 2

HCID 66982Decanoyl chlorideHCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

생성물 1

HCID 44626081(8R,9S,10R,13S,14S,17S)-13-ethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl decanoate수율 50.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매

실험 절차

Add decanoyl chloride (1.9 g.) to 13β-ethyl-17β-hydroxy-gon-4-en-3-one (1.3 g.) in pyridine (12.5 cc.) and allow the mixture to stand at room temperature overnight. Pour the mixture in 2N hydrochloric acid and extract with ether. Wash, dry and evaporate the extracts and recrystallize the residue from benzene-hexane to give the title compound (1.0 g.), m.p. 97°-97.5°; ultraviolet absorption peak at 239 mμ (ε16,500); infrared absorption peaks at 5.74; 5.99, 6.17 μ.

후처리

  1. extractionextract with ether
  2. washWash
  3. customdry
  4. customevaporate the extracts
  5. customrecrystallize the residue from benzene-hexane

출처 및 근거

ORD 기록
ord-26ff28a40a344a6a84d5c76a985b2805
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03959322

연결된 노트

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