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

HRID 2414303Notes

Reaction equation

HRID 2414303 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 and 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
  6. addition1 mL of 5N HCl was added
  7. customThe solvents were removed by evaporation
  8. customthe product crystallized from EtOAc

Sources & evidence

ORD record
ord-354c64350d50427690f7d9092ff3a4f6
Source dataset
uspto-grants-2004_11
Patent number
US06812244B2

Reaction notes

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