Hydrochloric Acid → Ethyl 2-(1-benzylcyclohexyl)-2-cyanoacetate

HRID 1886898Notes

Reaction equation

HRID 1886898 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([C:12](=[C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].Cl>C(OCC)C>[CH2:1]([C:18]1([CH:12]([C:10]#[N:11])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 81256Ethyl cyanocyclohexylideneacetateHCID 178418336HCID 178418336, compound

Product 1

HCID 14435569Ethyl 2-(1-benzylcyclohexyl)-2-cyanoacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1 M Benzylmagnesium chloride in diethyl ether (18.92 ml) was added dropwise to ethyl 2-cyano-2-cyclohexylideneacetate (1.828 g, 9.46 mmol) in diethyl ether (6.31 ml) at 23° C. The mixture was stirred at room temperature for 3 days. Then 10% hydrochloric acid (7.83 ml, 255 mmol) was added dropwise at 0° C. while stirring. The organic layer was separated, washed with water, dried over Na2SO4, filtered, and concentrated.

Workup

  1. stirringwhile stirring
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38c9284ead934dc5b600d20cbdad8608
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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