Tributylamine → HCID 54034270, compound

HRID 1156467Notes

Reaction equation

HRID 1156467 reaction equation
[C:1]1([C:14](Cl)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](Cl)=O)=[CH:3][CH:2]=1.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=C.C(N(CC[CH2:35][CH3:36])CCCC)CCC>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:22]([O:21][C:17]([CH:18]=[CH:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]([CH:14]=[CH:18][C:17]([O:21][CH2:35][CH3:36])=[O:20])=[CH:2][CH:3]=1)=[O:20])[CH3:23]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 8821Ethyl AcrylateHCID 12782416HCID 12782416, compound

Product 1

HCID 54034270HCID 54034270, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

0.0561 g (0.25 millimol) of palladium acetate, 3.16 g (12.5 millimols) of naphthalene-1,4-dicarboxylic acid dichloride, 3.12 g (31.25 millimols) of ethyl acrylate and 4.63 g (25 millimols) of tri-n-butylamine in 150 ml of p-xylene are stirred for 2 hours at 120° C. The crude product is chromatographed on silica gel in methylene chloride, and then recrystallised from cyclohexane. 2.31 g (57% of theory) of pale yellow crystals, of melting point 90°-91° C., are obtained. Analysis for C20H20O4 : calculated C 74.06%, H 6.22%, O 19.73%; found C 74.04%, H 6.17%, O 19.72%.

Workup

  1. customThe crude product is chromatographed on silica gel in methylene chloride
  2. customrecrystallised from cyclohexane
  3. custom2.31 g (57% of theory) of pale yellow crystals, of melting point 90°-91° C., are obtained

Sources & evidence

ORD record
ord-16f0fb74a1fc4899ab6d136db88000f1
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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