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

HRID 1464739ノート

反応式

HRID 1464739 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-bec18076e81d4c15b454886083fdc14f
出典データセット
uspto-grants-1994_04
特許番号
US05306728

反応ノート

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