Iodoethane → HCID 22996220, compound

HRID 1167317Notes

Reaction equation

HRID 1167317 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:12][O:13][CH3:14])[CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21](I)[CH3:22]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH2:12][O:13][CH3:14])[CH:11]=1)[C:6]([O:8][CH2:21][CH3:22])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 21942607HCID 21942607, compound

Product 1

HCID 22996220HCID 22996220, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-cyano-5-methoxymethyl-benzoic acid (90 mg, 0.469 mmol) in acetonitrile (3 mL) was added cesium carbonate (199 mg, 0.1 mmol) and ethyl iodide (44 μL, 0.563 mmol), respectively. The reaction mixture was stirred at reflux for 4 h. Upon cooling to room temperature, the reaction mixture was filtered and the filtrated was concentrated in vacuo. The residue was taken up in ethyl acetate and washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo to afford ethyl 3-cyano-5-methoxymethyl-benzoate (88 mg, 70%).

Workup

  1. temperatureat reflux for 4 h
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrated was concentrated in vacuo
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solid was then filtered off
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-593e2425a3334f8a9a3b934eaa8638d9
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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