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

HRID 1069049

反応式

HRID 1069049 の反応式
[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]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8955PregnenoloneHCID 516892Sodium Bicarbonate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8023Ethyl vinyl ether溶媒

実験手順

—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.

後処理

  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

出典と根拠

ORDレコード
ord-961e77002bc44415953e0afe8929298c
出典データセット
uspto-grants-2001_06
特許番号
US06251887B1

関連ノート

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