Cesium carbonate → HCID 53638138, compound

HRID 1421745Notes

Reaction equation

HRID 1421745 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.[CH2:14](Cl)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2314961-Chloro-2-phenylethaneHCID 16641129Methyl 4-cyano-3-hydroxybenzoate

Product 1

HCID 53638138HCID 53638138, 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 (8.5 ml) and treated with phenethylchloride (224 μl, 1.7 mmol). Cs2CO3 (610 mg, 1.87 mmol) was then added and the reaction mixture stirred at room temp. for 16 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 the 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-9b6068b403164cfcb02fa4c6a778bb69
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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