Tributylamine → HCID 66691768, compound

HRID 330821

Reaction equation

HRID 330821 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].[CH2:19]([O:21][CH:22]([O:25]CC)[CH:23]=[CH2:24])[CH3:20].C(N(CCCC)CCCC)CCC.CCOC(C)=O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][CH2:24][C:15]1[CH:16]=[CH:17][C:12]([C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:13][CH:14]=1)[CH3:20]

Participants

8

Reactant 4

HCID 7622TributylamineHCID 8857Ethyl AcetateHCID 624773,3-Diethoxy-1-propene2×HCID 66691575HCID 66691575, compound

Product 1

HCID 66691768HCID 66691768, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To 1.80 g (5.17 mmol) 1-ethoxy-4-((4-iodophenyl)ethynyl)benzene (XII.1) in 24 mL DMF are added 2.36 mL (15.5 mmol) 3,3-diethoxy-propene, 3.69 mL (15.5 mmol) tributylamine, 1.44 g (5.17 mmol) tetrabutylammoniumchloride and 0.04 g (0.16 mmol) palladium(II)acetate under argon. The mixture is stirred at 120° C. for 12 h. After that time, 1.18 mL (7.76 mmol) 3,3-diethoxy-propene are added and the mixture is stirred at 120° C. for 5 d. After cooling, EtOAc is added and the mixture is washed with 1N potassium hydrogensulfate solution and water. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; PE:DCM 1:1) to yield the desired product.

Workup

  1. stirringthe mixture is stirred at 120° C. for 5 d
  2. temperatureAfter cooling
  3. washthe mixture is washed with 1N potassium hydrogensulfate solution and water
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. customthe solvent is evaporated
  6. customThe residue is purified by column chromatography (silica gel; PE:DCM 1:1)

Sources & evidence

ORD record
ord-caeaae0a8b5941e9b57e00af235f045f
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Linked notes

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