Diethylamine → HCID 86746608, compound

HRID 1613313Notes

Reaction equation

HRID 1613313 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(NCC)C.Br[C:15]1[CH:16]=[C:17]([CH:24]=[CH:25][CH:26]=1)/[CH:18]=[CH:19]\[C:20]([O:22][CH3:23])=[O:21]>Cl[Pd](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>[C:17]1(/[C:18](/[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:19]\[C:20]([O:22][CH3:23])=[O:21])[CH:24]=[CH:25][CH:26]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 10821PhenylacetyleneHCID 86746609Methyl (2Z)-3-(3-bromophenyl)-2-propenoate

Product 1

HCID 86746608HCID 86746608, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

0.158 g of cuprous iodide and 0.424 g of phenylacetylene were added to 25 ml of a diethylamine solution containing 1.000 g of methyl (Z)-3-bromocinnamate and 0.029 g of bis(triphenylphosphine)dichloropalladium. The mixture was then stirred for 1 hour at room temperature, after which the solvent was distilled off under reduced pressure. Water was added to the residue, and the resulting mixture was extracted twice with benzene. The combined benzene extracts were washed with water, dried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel (70-230 Tyler mesh, 25 g). Those fractions eluted with a 39:1 by volume mixture of hexane and ethyl acetate were collected to afford 1.043 g of the title compound, melting at 73°-75° C. (after recrystallisation from hexane).

Workup

  1. distillationafter which the solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe resulting mixture was extracted twice with benzene
  4. washThe combined benzene extracts were washed with water
  5. dry with materialdried over anhydrous sodium sulfate and condensed by evaporation under reduced pressure
  6. washThose fractions eluted with a 39:1 by volume mixture of hexane and ethyl acetate
  7. customwere collected
  8. customto afford
  9. custom1.043 g of the title compound, melting at 73°-75° C. (after recrystallisation from hexane)

Sources & evidence

ORD record
ord-56b3108745cc44c58eb12310a49ea042
Source dataset
uspto-grants-1993_03
Patent number
US05192766

Reaction notes

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