Ethanol → HCID 22282620, compound

HRID 2085338Notes

Reaction equation

HRID 2085338 reaction equation
FC(S([C:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][CH2:10][CH:9]=1)(=O)=O)(F)F.[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>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:8]([C:21]2[CH:22]=[CH:23][C:18]([C:24]([O:28][CH3:27])=[O:35])=[CH:19][CH:20]=2)=[CH:9][CH2:10]1

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 69799609HCID 69799609, compound

Product 1

HCID 22282620HCID 22282620, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

2H-1-benzothiopyran-4-yl trifluoromethyl sulfone from reaction 33a (1.83 g, 6.17 mmol) and 4-(methoxy carbonylphenyl)boronic acid (1.11 g, 6.17 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 (4.66 mL, 12.35 mmol) were added. Nitrogen was bubbled through the reaction for 15 minutes tetrakis(triphenylphosphine)-palladium(0) (0.35 g, 0.31 mmol) was added. The reaction was heated to reflux for 2 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 acetate:hexane (15:85, v:v) to give methyl 4-(2H-1-benzothiopyran-4-yl)benzoate (1.75 g, 67%) as a solid.

Workup

  1. customat room temperature
  2. additionwas added
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 2 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 acetate:hexane (15:85, v:v)

Sources & evidence

ORD record
ord-7a5350d4abc2474c95a7a221078cdaf4
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

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