Cesium carbonate → HCID 54500758, compound

HRID 1421748Notes

Reaction equation

HRID 1421748 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([OH:12])[CH:5]=1.[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([O:12][CH2:23][CH2:22][CH2:21][CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78543(4-Chlorobutyl)benzeneHCID 16641129Methyl 4-cyano-3-hydroxybenzoate

Product 1

HCID 54500758HCID 54500758, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Cyano-3-hydroxybenzoic acid methyl ester, Example 34 Step 3 (300 mg, 1.7 mmol) was dissolved in DMF (85 ml) and treated with phenylbutylchloride (287 mg, 1.7 mmol). Cs2CO3 (610 mg, 1.87 mmol) was then added and the reaction mixture stirred at room temp. for 18 hours. The mixture was filtered and washed with DMF (3×10 mL). The solvent was removed in vacuo and the residue was purified by flash chromatography (10% EtOAc/Hexane) to yield desired product.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with DMF (3×10 mL)
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-bea1ed27dbf54b2eb3f073c28bd79230
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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