Water → Pregn-5-en-20-yn-3-one, 17-hydroxy-, cyclic 1,2-ethanediyl acetal, (17alpha)-

HRID 2057506

반응식

HRID 2057506 반응식
CO[CH:3]([O:6][CH3:7])[O:4][CH3:5].[CH3:8][C@@:9]12[C@H:19]3[CH2:20][CH2:21][C@:22]4([CH3:30])[C@:26]([OH:29])([C:27]#[CH:28])[CH2:25][CH2:24][C@H:23]4[C@@H:18]3[CH2:17][CH2:16][C:15]1=[CH:14]C(=O)[CH2:11][CH2:10]2.O.C([O-])(=O)C.[Na+]>C(O)CO.CO>[CH2:7]1[CH2:5][O:4][C:3]2([CH2:11][CH2:10][C@@:9]3([CH3:8])[C:15](=[CH:16][CH2:17][C@@H:18]4[C@@H:19]3[CH2:20][CH2:21][C@@:22]3([CH3:30])[C@H:23]4[CH2:24][CH2:25][C@@:26]3([OH:29])[C:27]#[CH:28])[CH2:14]2)[O:6]1

참가 물질

7

반응물 4

HCID 962WaterHCID 9005Trimethyl orthoformateHCID 517045Sodium AcetateHCID 5284557Ethisterone

생성물 1

HCID 12922974Pregn-5-en-20-yn-3-one, 17-hydroxy-, cyclic 1,2-ethanediyl acetal, (17alpha)-

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 887Methanol용매

실험 절차

Trimethylorthoformate (20 ml.) and p-TSA monohydrate (1.9 g.) is added to a slurry of ethisterone (I, 31.34 g.) in ethylene glycol (100 ml.) and methanol (200 ml.). The mixture is heated to 50° until the reaction is complete (about 5 hours) as measured by TLC. The mixture is cooled to 5° and water (200 ml.) containing sodium acetate (6.6 g.) is added. The resulting suspension is filtered to recover the solids which are dried at 50° under reduced pressure (20 mm) for 6 hours to give the title compound, m.p. 245°-250°; NMR (CDCl3) 0.87, 1.03, 2.57, 3.97 and 5.23δ.

후처리

  1. temperatureThe mixture is heated to 50° until the reaction
  2. custom(about 5 hours)
  3. temperatureThe mixture is cooled to 5°
  4. additionis added
  5. filtrationThe resulting suspension is filtered
  6. customto recover the solids which
  7. customare dried at 50° under reduced pressure (20 mm) for 6 hours

출처 및 근거

ORD 기록
ord-dcfffbe7d2384d7cb2638c4c25db385f
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04211701

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