Dimethylformamide → HCID 66765522, compound

HRID 402775Notes

Reaction equation

HRID 402775 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[C:8]2[OH:18].C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:26][CH3:27].CN(C=O)C>CCOC(C)=O>[CH2:26]([O:18][C:8]1[C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[CH:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=1)[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 12113351HCID 12113351, compound

Product 1

HCID 66765522HCID 66765522, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a 25 mL round bottom flask were added ethyl 8-methoxy-4-hydroxynaphthalene-2-carboxylate (0.25 g, 1.02 mmol), Cs2CO3 (0.33 g, 1.02 mmol), iodoethane (0.79 g, 5.1 mmol) and DMF (4 mL). The resulting reaction mixture was stirred at 70° C. overnight. After cooling to room temperature, the reaction was diluted with EtOAc (30 mL), washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified on a silica gel column eluting with a gradient of 10-20% EtOAc/hexanes to give the title intermediate (0.19 g) as a light yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified on a silica gel column
  8. washeluting with a gradient of 10-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-dedd73bfe3f5415da0bc0c9a470a09e8
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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