Potassium Phosphate, Tribasic → HCID 66760548, compound

HRID 1850422Notes

Reaction equation

HRID 1850422 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][C:10]1([CH3:20])[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([CH3:19])[C:12]=2[O:11]1.B([O-])([O-])O[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1>Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:9][C:10]1([CH3:20])[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)=[C:18]([CH3:19])[C:12]=2[O:11]1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 141573Benzofuran, 2,3-dihydro-2,2,7-trimethyl-HCID 866453334-Methylphenyl borate

Product 1

HCID 66760548HCID 66760548, compoundYield 943.9%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 178418751HCID 178418751, compoundCatalystHCID 1140TolueneSolvent

Procedure

Tripotassium phosphate (28.1 g, 132 mmol) was added to a solution of toluene (200 mL) containing 2,2,7-trimethyl-2,3-dihydro-1-benzofuran (10.0 g, 5.08 mmol) synthesized in Reference Example 155, bis(triphenylphosphine)nickel (II) dichloride (0.998 g, 1.53 mmol), triphenylphosphine (0.800 g, 3.05 mmol) and 4-methylphenyl borate (8.99 g, 66.1 mmol), and the mixture was stirred under heated reflux for 2 hours. After cooled to room temperature, the reaction solution was filtered using Celite. Water was added to the obtained filtrate, and it was subjected to extraction using ethyl acetate. The extract was dried using anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. After that, the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 20:1) to give 12.1 g of the title compound as a brown solid (yield: 94%).

Workup

  1. temperatureunder heated
  2. temperaturereflux for 2 hours
  3. filtrationthe reaction solution was filtered
  4. additionWater was added to the obtained filtrate, and it
  5. extractionwas subjected to extraction
  6. customThe extract was dried
  7. customthe solvent was removed under reduced pressure
  8. customAfter that, the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 20:1)

Sources & evidence

ORD record
ord-b380f402ca2b4eff8218b97d2890ed12
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

Loading…