Tetrahydrofuran → 2-(Ethyl(1-ethynylcyclohexyl)amino)ethan-1-ol

HRID 347213

Reaktionsgleichung

Reaktionsgleichung von HRID 347213
[CH2:1]([NH:3][CH:4](O)[CH3:5])[CH3:2].C(O[C:11]1([C:17]#[CH:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)(=O)C.C1C[O:22]CC1>Cl[Cu]>[CH2:1]([N:3]([C:11]1([C:17]#[CH:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:4][CH2:5][OH:22])[CH3:2]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 78903Cyclohexanol, 1-ethynyl-, 1-acetateHCID 18179409Ethylaminoethanol

Produkt 1

HCID 223141892-(Ethyl(1-ethynylcyclohexyl)amino)ethan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 62652Cuprous chlorideKatalysator

Versuchsvorschrift

To 1.17 ml (12 mmo) ethylaminoethanol in 8 ml THF were added 29.8 mg (0.3 mmol) CuCl, followed by 1 g (6.02 mmol) 1-ethynylcyclohexyl acetate. The solution was stirred at RT for 3 h, the solvent was removed and the residue dissolved in ether/2M HCl. The phases were separated, and after addition of NaOH (pH11) to the aqueous phase, it was extracted with ether. The ether phase was dried over Na2SO4 and concentrated. Distillation by Kugelrohr yielded 2-[Ethyl-(1-ethynyl-cyclohexyl)-amino]-ethanol as colorless oil, MS: 196 (MH+).

Aufarbeitung

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in ether/2M HCl
  3. customThe phases were separated
  4. additionafter addition of NaOH (pH11) to the aqueous phase, it
  5. extractionwas extracted with ether
  6. dry with materialThe ether phase was dried over Na2SO4
  7. concentrationconcentrated
  8. distillationDistillation by Kugelrohr

Quellen und Nachweise

ORD-Eintrag
ord-812a42b562b4483992146eccdf850e9a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173043B2

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