Potassium Carbonate → Benzo(b)naphtho(1,2-d)furan

HRID 1189601Notes

Reaction equation

HRID 1189601 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[OH:18].CN1CCCC1=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH:16]1[C:17]2[C:8]3[C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[O:18][C:9]=3[CH:10]=[CH:11][C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 50992704HCID 50992704, compound

Product 1

HCID 268932Benzo(b)naphtho(1,2-d)furanYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Into a 1 L three-neck flask were placed 15 g (63 mmol) of 1-(2-fluorophenyl)-2-naphthol, 300 mL of N-methyl-2-pyrrolidone (NMP), and 18 g (130 mmol) of potassium carbonate. The mixture in this flask was stirred at 150° C. for 6 hours under a nitrogen stream. After that, this mixture was cooled down to room temperature and added to about 500 mL of water. The aqueous layer of this mixture was subjected to extraction with ethyl acetate, and the obtained solution of the extract and the organic layer were combined and washed with water and saturated brine. The organic layer was dried with magnesium sulfate, and after that, this mixture was gravity-filtered. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (developing solvent: hexane) to give an oily substance. The obtained oily substance was dried under reduced pressure, so that 11.8 g of a colorless transparent oily substance of the object of the synthesis was obtained in 86% yield. The reaction scheme of Step 2 is illustrated in (E1-2).

Workup

  1. customInto a 1 L three-neck flask were placed
  2. temperatureAfter that, this mixture was cooled down to room temperature
  3. extractionThe aqueous layer of this mixture was subjected to extraction with ethyl acetate
  4. extractionthe obtained solution of the extract
  5. washwashed with water and saturated brine
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationafter that, this mixture was gravity-filtered
  8. concentrationThe obtained filtrate was concentrated
  9. customto give an oily substance
  10. customThe obtained oily substance was purified by silica gel column chromatography (developing solvent: hexane)
  11. customto give an oily substance
  12. customThe obtained oily substance was dried under reduced pressure, so that 11.8 g of a colorless transparent oily substance of the object of the synthesis
  13. customwas obtained in 86% yield
  14. customThe reaction scheme of Step 2

Sources & evidence

ORD record
ord-202fae5bc9d844e1976f03d393424b75
Source dataset
uspto-grants-2014_03
Patent number
US08674117B2

Reaction notes

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