N,N-Dimethylaniline → 16beta-Ethyl-17beta-(2-bromopropionyloxy)-4-estren-3-one

HRID 64705

反応式

HRID 64705 の反応式
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:22])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].CN(C)C1C=CC=CC=1.[Br:32][CH:33]([CH3:37])[C:34](Br)=[O:35].C(OCC)(=O)C>ClCCl>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:34](=[O:35])[CH:33]([Br:32])[CH3:37])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

参加物

6

反応物 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 79047Propanoyl bromide, 2-bromo-HCID 443947Oxendolone

生成物 1

HCID 8674097916beta-Ethyl-17beta-(2-bromopropionyloxy)-4-estren-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In 70 ml of dichloromethane are dissolved 3.0 g of 16β-ethyl-17β-hydroxy-4-estren-3-one and 1.6 ml of N,N-dimethylaniline and, with stirring, 1.2 ml of α-bromopropionyl bromide is added to the above solution. The mixture is stirred at room temperature (15°-25° C.) for 30 hours followed by addition of 300 ml of ethyl acetate. The mixture is washed with 10% sulfuric acid and saturated aqueous sodium chloride solution in that order and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 300 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 600 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 2.7 g of the above-identified compound as a light-yellow viscous oil.

後処理

  1. stirringThe mixture is stirred at room temperature (15°-25° C.) for 30 hours
  2. washThe mixture is washed with 10% sulfuric acid and saturated aqueous sodium chloride solution in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. washpassage of 300 ml of diisopropyl ether-n-hexane (1:1), elution
  6. customThe eluate is evaporated under reduced pressure
  7. customto remove the solvent

出典と根拠

ORDレコード
ord-f6b3b723c1f442e696db14178b654489
出典データセット
uspto-grants-1986_09
特許番号
US04609650

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