Tributylamine → 2,6-Bis-(2-ethoxycarbonylvinyl)-naphthalene

HRID 1156466

Reaction equation

HRID 1156466 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](Cl)=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:14](Cl)=O.[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:7]1[CH:8]=[CH:9][C:10]2[C:5](=[CH:4][CH:3]=[C:2]([CH:14]=[CH:18][C:17]([O:21][CH2:35][CH3:36])=[O:20])[CH:1]=2)[CH:6]=1)=[O:20])[CH3:23]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 8821Ethyl AcrylateHCID 34855962,6-Naphthalenedicarbonyl dichloride

Product 1

HCID 539866572,6-Bis-(2-ethoxycarbonylvinyl)-naphthalene

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

0.1683 g (0.75 millimol) of palladium acetate, 9.49 g (37.5 millimols) of naphthalene-2,6-dicarboxylic acid dichloride, 9.38 g (93.75 millimols) of ethyl acrylate and 13.89 g (75 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 is then recrystallised from cyclohexane. 4.11 g (34% of theory) of yellow crystals, of melting point 150°-51° C., are obtained. Analysis for C20H20O4 : calculated C 74.06%, H 6.22%, O 19.73%; found C 73.85%, H 6.41%, O 19.56%.

Workup

  1. customThe crude product is chromatographed on silica gel in methylene chloride
  2. customis then recrystallised from cyclohexane
  3. custom4.11 g (34% of theory) of yellow crystals, of melting point 150°-51° C., are obtained

Sources & evidence

ORD record
ord-d988aad96d9d4a799f71da63ad3ef627
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Linked notes

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