Ethyl Acetate → 4-(2,3-Dihydro[1,4]benzodioxin-5-yl)pyridine

HRID 619110Notes

Reaction equation

HRID 619110 reaction equation
C(B(CC)[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)C.Br[C:13]1[C:22]2[O:21][CH2:20][CH2:19][O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.[OH-].[K+].C(OCC)(=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.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:18]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:4]3[CH:5]=[CH:6][N:7]=[CH:8][CH:9]=3)[C:22]=2[O:21][CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 133188714-(Diethylboranyl)pyridineHCID 187872685-Bromo-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 109327794-(2,3-Dihydro[1,4]benzodioxin-5-yl)pyridine

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

14.7 mmol of diethyl(pyrid-4-yl)borane, 22 mmol of 5-bromo-2,3-dihydro[1,4]-benzodioxine, 44.1 mol of KOH in powder form, 7.4 mmol of tetrabutylammonium bromide and 0.74 mmol of tetrakis(triphenylphosphine)palladium in 75 ml of tetrahydrofuran are mixed at room temperature, and the mixture is then refluxed for 24 hours. 225 ml of ethyl acetate are added and the mixture is washed with a saturated sodium chloride solution. Drying is carried out over MgSO4, followed by evaporation and purification over a silica column (eluant CH2Cl2, then CH2Cl2 /CH3COOC2H5 80/20).

Workup

  1. temperaturethe mixture is then refluxed for 24 hours
  2. washthe mixture is washed with a saturated sodium chloride solution
  3. customDrying
  4. customfollowed by evaporation and purification over a silica column (eluant CH2Cl2

Sources & evidence

ORD record
ord-993d64b180db49fb869688791ce26725
Source dataset
uspto-grants-1999_09
Patent number
US05958927

Reaction notes

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