Ethyl cyanoformate → Ethyl 4-ethoxy-2-oxocyclohex-3-ene-1-carboxylate

HRID 1917263

Reaction equation

HRID 1917263 reaction equation
[Li+].CC([N-]C(C)C)C.[CH2:9]([O:11][C:12]1[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH:13]=1)[CH3:10].C([C:21]([O:23][CH2:24][CH3:25])=[O:22])#N>C1COCC1>[CH2:24]([O:23][C:21]([CH:15]1[CH2:16][CH2:17][C:12]([O:11][CH2:9][CH3:10])=[CH:13][C:14]1=[O:18])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 69336Ethyl cyanoformateHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 58997709Ethyl 4-ethoxy-2-oxocyclohex-3-ene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of LDA (192 mmol) in THF (200 mL) was added 3-ethoxy-cyclohex-2-enone (23 mL) dropwise. After stirring for 1 h at −78° C., ethyl cyanoformate (16 mL) was added. The mixture was stirred at −78° C. for 4 h and then was warmed to rt and stirred for 1 h. The mixture was concentrated, diluted with aq. NH4Cl (300 mL), and poured into water. The resulting solids were collected by suction filtration and washed with hexanes followed by water, then was dried and concentrated to provide 17.1 g of a brown solid. TLC (SiO2, 33% EtOAc/hexanes): Rf=0.43.

Workup

  1. stirringThe mixture was stirred at −78° C. for 4 h
  2. temperaturewas warmed to rt
  3. stirringstirred for 1 h
  4. concentrationThe mixture was concentrated
  5. additiondiluted with aq. NH4Cl (300 mL)
  6. additionpoured into water
  7. filtrationThe resulting solids were collected by suction filtration
  8. washwashed with hexanes
  9. customwas dried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bbcc19a53b1445139b5e11a48fa3fafd
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Linked notes

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