Dimethylformamide → 2,7-Diacetylnaphthalene

HRID 1640352Notes

Reaction equation

HRID 1640352 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11](OS(C(F)(F)F)(=O)=O)=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.C([O:29][CH2:30][CH2:31]CC)=C.C(N([CH2:39][CH3:40])CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=[O:73]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:39]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:30](=[O:29])[CH3:31])=[CH:12][CH:13]=2)[CH:8]=1)(=[O:73])[CH3:40]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 109387851,1'-(2,7-Naphthalenediyl) bis(1,1,1-trifluoromethanesulfonate)

Product 1

HCID 156863122,7-Diacetylnaphthalene

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

54.0 g of 2,7-dihydroxynaphthalene was dissolved in a mixture of 680 ml of dichloromethane and 136 ml of pyridine, and to this, 228 g of trifluoromethanesulfonic anhydride (produced by TOKYO CHEMICAL INDUSTRY CO., LTD.) was added dropwise at 0° C. After the resulting mixture was reacted at 5° C. for 2 hours and then at room temperature for one day, a reactant was treated by a normal method to obtain 143 g of 2,7-bis(trifluoromethane sulfonyloxy)naphthalene. 143 g of this 2,7-bis(trifluoromethane sulfonyloxy)naphthalene was mixed with 216 ml of n-butyl vinyl ether, 113 ml of triethylamine, 2.78 g of 1,3-bis(diphenylphosphino)propane, 0.76 g of palladium acetate and 680 ml of dimethylformamide and the resulting mixture was reacted at 70 to 85° C. for two days. The reactant was treated by a normal method to obtain 40 g of 2,7-diacetylnaphthalene. 4.62 g of this 2,7-diacetylnaphthalene was reacted with 7.87 g of 8-amino-7-quinoline carboaldehyde and 7.9 g of potassium hydroxide in 220 ml of ethanol at 60° C. and a reactant was treated by a normal method to obtain 4.44 g of 2,7-di(1,10-phenanthroline-2-yl)naphthalene. 5.48 g of this 2,7-di(1,10-phenanthroline-2-yl)naphthalene was reacted with 22.6 ml of phenyl lithium (2.0 M cyclohexane-ether solution) in 200 ml of toluene at room temperature for 2 days and a reactant was treated by a normal method. The obtained product was reacted with 100 g of manganese dioxide in 400 ml of dichloromethane at room temperature for 2.5 hours and a reactant was treated by a normal method to obtain 0.93 g of E-57.

Workup

  1. customthe resulting mixture was reacted at 70 to 85° C. for two days
  2. additionThe reactant was treated by a normal method

Sources & evidence

ORD record
ord-8e77ad773fa3442681490923e54b2885
Source dataset
uspto-grants-2012_02
Patent number
US08114529B2

Reaction notes

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