Dichloromethane → (3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

HRID 1069049

반응식

HRID 1069049 반응식
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.C(N([CH2:29][CH3:30])CC)C.[C:31](=[O:34])([O-])O.[Na+].Cl[CH2:37]Cl>C(OCC)=C>[CH2:31]([O:34][CH:29]([O:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)[CH3:30])[CH3:37]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8955PregnenoloneHCID 516892Sodium Bicarbonate

생성물 1

HCID 54547839(3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

시약·촉매·용매 1

HCID 8023Ethyl vinyl ether용매

실험 절차

—Pyridium p-toluenesulfonate (6.32 g) was added to a solution of (3β)-3-hydroxypregn-5-en-20-one (1; 100 g) in dichloromethane (600 ml) and ethyl vinyl ether (200 ml). After stirring of the reaction mixture for 1 h at room temperature triethylamine (20 ml) was added, whereupon the mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate (1 l). The product was extracted into dichloromethane; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-one (2; 125.6 g), which was used in the following step without further purification.

후처리

  1. additionwas added, whereupon the mixture
  2. extractionThe product was extracted into dichloromethane
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-961e77002bc44415953e0afe8929298c
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251887B1

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