Tetrahydrofuran → HCID 58220559, compound

HRID 2358914Notes

Reaction equation

HRID 2358914 reaction equation
[OH-].[K+].[CH2:3]1COC[CH2:4]1.[CH:8]1[C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][C:12]=2[C:11](B(O)O)=[CH:10][CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C(OC(=O)C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO.ClCCl>[CH:3]([C:11]1[C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[C:16]=2[CH:8]=[CH:9][CH:10]=1)=[CH2:4]

Participants

10

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 58220559HCID 58220559, compoundYield 42%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

16.09 g (0.259 mol) of Potassium hydroxide (86%) are placed in a 500 ml three necked round bottomed flask equipped with a magnetic stirrer and a reflux condenser. 200 ml of THF and 6.5 ml of Dichloromethane are added. The mixture is refluxed. After 1 hour the mixture is cooled to room temperature. A solution of 8 g (37.74 mmol) dibenzofuran-4-boronic acid, 0.8 g (3.02 mmol) of Triphenylphosphine, 339 mg (0.7 mmol) of Palladium (II) acetate and 200 ml of Methanol are added. The reaction mixture is heated to 60° C. internal temperature. After 2 hours the reaction is complete and cooled down to room temperature. The mixture is diluted with H2O and Ethylacetate. The organic phase is extracted twice with water and once with brine. The organic phase is dried over Sodiumsulfate and the solvent evaporated. The crude product is purified by column chromatography (Heptane). 4-Vinyl-dibenzofuran is isolated in 42% yield.

Workup

  1. customequipped with a magnetic stirrer and a reflux condenser
  2. temperatureThe mixture is refluxed
  3. temperatureThe reaction mixture is heated to 60° C. internal temperature
  4. temperaturecooled down to room temperature
  5. extractionThe organic phase is extracted twice with water and once with brine
  6. dry with materialThe organic phase is dried over Sodiumsulfate
  7. customthe solvent evaporated
  8. customThe crude product is purified by column chromatography (Heptane)

Sources & evidence

ORD record
ord-204c9193d92d4364a927c2c4dc7ca029
Source dataset
uspto-grants-2014_04
Patent number
US08685541B2

Reaction notes

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