Hydrochloric Acid → HCID 12686974, compound

HRID 331696Notes

Reaction equation

HRID 331696 reaction equation
I[C:2]1[CH:3]=[C:4]([O:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O.Cl>CS(C)=O.[Cu]I>[C:10]([CH:12]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 69839Benzene, 1-iodo-3-methoxy-HCID 145742L-Proline

Product 1

HCID 12686974HCID 12686974, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-iodoanisole (11.2 ml, 85 mmol), ethyl cyanoacetate (27.3 ml, 256 mmol), potassium carbonate (47.2 g, 342 mmol), copper(I) iodide (1.63 g, 8.55 mmol) and L-proline (1.97 g, 17.1 mmol) in dimethylsulfoxide (300 ml) was heated to 90° C. under argon for 11 h and then at room temperature over night. The solution was poured into 1N hydrochloric acid, extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium bicarbonate, filtered and the solvent evaporated to obtain a brown oil. Purification on 12 g SiO2 using 20% ethyl acetate in cyclohexane afforded a clear oil m=16.8 g (44.8%)

Workup

  1. waitat room temperature over night
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium bicarbonate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customto obtain a brown oil
  8. customPurification on 12 g SiO2 using 20% ethyl acetate in cyclohexane
  9. customafforded a clear oil m=16.8 g (44.8%)

Sources & evidence

ORD record
ord-7896107bd23143038f85d9aae285ed7d
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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