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

HRID 966342

Reaction equation

HRID 966342 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

To 1.17 ml (12 mmol) 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 (pH 11) to the aqueous phase, it was extracted with ether. The ether phase was dried over Na2SO4 and concentrated. Destillation by Kugelrohr yielded 2-[Ethyl-(1-ethynyl-cydohexyl)-amino]-ethanol as colorless oil, MS: 196 (MH+).

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in ether/2M HCl
  3. customThe phases were separated
  4. additionafter addition of NaOH (pH 11) to the aqueous phase, it
  5. extractionwas extracted with ether
  6. dry with materialThe ether phase was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39d69bb7d8b94684b0b7cd8bd0251890
Source dataset
uspto-grants-2005_10
Patent number
US06951879B2

Linked notes

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