Cesium carbonate → HCID 17984322, compound

HRID 1181035Notes

Reaction equation

HRID 1181035 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:20][CH:21](Br)[CH3:22]>CN(C=O)C>[Br:20][CH2:21][CH2:22][O:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 112011,1-DibromoethaneHCID 2886346-Methoxy-2-naphthol

Product 1

HCID 17984322HCID 17984322, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 6-methoxynaphthalen-2-ol (1.07 g, 6.14 mmol) in DMF (4 mL) were added cesium carbonate (3.11 g, 9.55 mmol) and dibromoethane (2.5 mL, 29 mmol). The mixture was stirred and heated at 55° C. for 48 h. The reaction mixture was cooled, filtered, diluted with EtOAc, and washed with brine (2×30 mL). The organic layer was dried (Na2SO4) and concentrated. The crude product was purified using radial chromatography (2:98 to 25:75 EtOAc:Hex) to give the title compound as a white solid (0.52 g, 30%): 1H NMR (400 MHz, CDCl3) δ 3.61 (t, J=6.1 Hz, 2H), 3.82 (s, 3H), 4.30 (t, J=6.4 Hz, 2H), 7.01-7.08 (m, 4H), 7.56 (dd, J=12.0, 9.0 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additiondiluted with EtOAc
  4. washwashed with brine (2×30 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-d3ff1e5e7d0e4f82aceb889b0b49e77e
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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