Ethyl Acetate → Cyclohexane ethylacetate

HRID 1360366Notes

Reaction equation

HRID 1360366 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C.[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43]>C1COCC1>[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43].[CH2:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 21867204Cyclohexane ethylacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The amine AM17 (1 eq.) was initially introduced into the flask together with the corresponding acid (1 eq.) under nitrogen. TBTU (1 eq.) and HOBT (1 eq.) were then added and the solids were dissolved in THF (8.5 ml/mmol of amine). N-ethyldiisopropylamine (2 eq.) was added to this mixture with constant stirring and the mixture was subsequently stirred at room temperature overnight. Ethyl acetate was added to the reaction solution and the mixture was washed with sat. NaCl solution, NaHCO3 solution, NaCl and with NH4HSO3 solution and evaporated to dryness with nitrogen and the residue was dried overnight using an oil pump. It was possible to obtain the desired product by means of flash column chromatography (mobile phase: ethyl acetate/cyclohexane, 1:5).

Workup

  1. stirringthe mixture was subsequently stirred at room temperature overnight
  2. washthe mixture was washed with sat. NaCl solution, NaHCO3 solution, NaCl and with NH4HSO3 solution
  3. customevaporated to dryness with nitrogen
  4. customthe residue was dried overnight

Sources & evidence

ORD record
ord-b3bf246f724a4e20a4608a7367c0f83c
Source dataset
uspto-grants-2011_02
Patent number
US07879858B2

Reaction notes

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