N,N-Dimethylaniline → 16beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

HRID 64703

반응식

HRID 64703 반응식
[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][CH2:33][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])[CH2:33][Br:32])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

참가 물질

6

반응물 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 61147Bromoacetyl bromideHCID 443947Oxendolone

생성물 1

HCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one수율 74.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

In 40 ml of dichloromethane are dissolved 4.5 g of 16β-ethyl-17β-hydroxy-4-estren-3-one and 1.8 g of N,N-dimethylaniline and, with ice-cooling and stirring, a solution of 3.5 g of bromoacetyl bromide in 5 ml of dichloromethane is added dropwise to the above solution. The mixture is stirred with ice-cooling for 30 minutes and at room temperature (15°-25° C.) for 5 hours, and 200 ml of ethyl acetate is added. The mixture is washed with 10% cold sulfuric acid (three times), water and saturated aqueous sodium chloride solution in that order and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure. The residue is recrystallized from diisopropyl ether-petroleum ether (1:1) to give 4.7 g of the above-identified compound as colorless crystals.

후처리

  1. temperaturewith ice-cooling
  2. stirringThe mixture is stirred with ice-
  3. washThe mixture is washed with 10% cold sulfuric acid (three times), water and saturated aqueous sodium chloride solution in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent is then distilled off under reduced pressure
  6. customThe residue is recrystallized from diisopropyl ether-petroleum ether (1:1)

출처 및 근거

ORD 기록
ord-18bde555835b47f78c6ab8bfa5bd8bba
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609650

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