Ethanol → HCID 22282577, compound

HRID 2085343Notes

Reaction equation

HRID 2085343 reaction equation
FC(F)(F)S([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:9][CH2:8][CH:7]=1)(=O)=O.[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[Li+].[C:27](=O)([O-])[O-:28].[K+].[K+].C([OH:35])C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([C:21]2[CH:22]=[CH:23][C:18]([C:24]([O:28][CH3:27])=[O:35])=[CH:19][CH:20]=2)=[CH:7][CH2:8]1

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 22282626HCID 22282626, compound

Product 1

HCID 22282577HCID 22282577, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

4-[(trifluoromethyl)sulfonyl]-2H-chromene from reaction 34a (1.78 g, 6.47 mmol) and 4-(methoxy carbonylphenyl) boronic acid (1.0 g, 5.6 mmol) were dissolved in ethanol (15 mL) and toluene (30 mL) under nitrogen at room temperature. Then lithium chloride (0.52 g, 12.35 mmol) and 2.65 M potassium carbonate (4.2 mL, 11.0 mmol) were added. Nitrogen was bubbled through the reaction for 15 minutes before the tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.31 mmol) was added. The reaction was heated to reflux for 3 h, allowed to cool then partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried over magnesium sulfate, and was concentrated. The product was purified by chromatography on silica gel eluting with ethyl ether:hexane (20:80, v:v) to give methyl 4-(2H-chromen-4-yl)benzoate (1.53 g, 99%) as a yellow solid.

Workup

  1. customat room temperature
  2. additionwas added
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 3 h
  5. temperatureto cool
  6. customthen partitioned between ethyl acetate and water
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationwas concentrated
  10. customThe product was purified by chromatography on silica gel eluting with ethyl ether:hexane (20:80, v:v)

Sources & evidence

ORD record
ord-dcb3f6d973df4b319f6a74c6d1a21266
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

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