Diethyl Ether → (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-5-[3-(3-thienyl)phenoxy]-4-oxopentylamine

HRID 1464739노트

반응식

HRID 1464739 반응식
Br[CH2:2][CH2:3][CH2:4][C:5](=[O:19])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:9]=1.Cl.[CH2:21]([NH:23][CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:22].[I-].[K+].C(OCC)C>CN(C)C=O>[CH2:21]([N:23]([CH2:2][CH2:3][CH2:4][C:5](=[O:19])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:9]=1)[CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH3:22]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 4875Potassium IodideHCID 199169541-[3-(3-Thienyl)phenoxy]-5-bromo-2-pentanoneHCID 19917114(E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride

생성물 1

HCID 19917078(E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-5-[3-(3-thienyl)phenoxy]-4-oxopentylamine수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

50 mg of 5-bromo-1-[3-(3-thienyl)phenoxy]-2-pentanone was dissolved in 1.8 ml of dimethylformamide, and 125 mg of a (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride and 29 mg of potassium iodide were added. The mixture was stirred at 40° C. for 1 hour, and then ethyl ether and ice water were added. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [hexane→chloroform] to give 20 mg (yield 27%) of the captioned compound as a colorless oil.

후처리

  1. customThe organic layer was separated
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe desiccant was separated by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [hexane→chloroform]

출처 및 근거

ORD 기록
ord-bec18076e81d4c15b454886083fdc14f
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306728

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