Cesium carbonate → 1-(4-Hydroxyphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

HRID 2213165Notes

Reaction equation

HRID 2213165 reaction equation
Cl.ClCCN1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:11]([O-:14])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:14][C:6]1[CH:7]=[CH:8][C:9]([O:14][C:11]2[C:8]3[C:7](=[CH:6][C:11]([O:14][CH3:11])=[CH:10][CH:9]=3)[CH:8]=[CH:9][C:10]=2[C:8]2[CH:7]=[CH:6][CH:7]=[C:10]([O:14][CH3:11])[CH:9]=2)=[CH:10][CH:6]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

Product 1

HCID 120741751-(4-Hydroxyphenoxy)-2-(3-Methoxyphenyl)-6-MethoxynaphthaleneYield 320%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.5 g (4 mmol) of 1-(4-hydroxyphenoxy)-2-(3-methoxyphenyl)-6-methoxynaphthalene in 40 mL of DMF was prepared. To this solution was added 920 mg (5 mmol) of 2-chloroethylpiperidine hydrochloride and 5.2 g (16 mmol) of Cs2CO3, the reaction was stirred at ambient temperature under a nitrogen atmosphere for sixteen hours. The solvents were removed by evaporation and the residue partioned between water and EtOAc. The EtOAc layer was washed with water, then brine, dried with Na2SO4, and evaporated to dryness. The residue was dissolved in 10 mL of MeOH ane 1 mL of 5N HCl was added. The solvents were removed by evaporation and the product crystallized from EtOAc. This yielded 1.8 g of the title compound as a white solid, mp 161–162° C.

Workup

  1. customThe solvents were removed by evaporation
  2. washThe EtOAc layer was washed with water
  3. dry with materialbrine, dried with Na2SO4
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in 10 mL of MeOH ane 1 mL of 5N HCl
  6. additionwas added
  7. customThe solvents were removed by evaporation
  8. customthe product crystallized from EtOAc

Sources & evidence

ORD record
ord-cebf7bf1d78d41b9b2c6cf64f211fa85
Source dataset
uspto-grants-2006_09
Patent number
US07105541B2

Reaction notes

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