Triethylamine → HCID 18372966, compound

HRID 375918Notes

Reaction equation

HRID 375918 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Br[C:14]1[S:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=1.C(N(CC)CC)C>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[C:1]([C:15]1[CH:16]=[C:17]([CH:19]=[O:20])[S:18][CH:14]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 698211-DodecyneHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 18372966HCID 18372966, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-dodecyne (23.9 g), 5-bromo-2-thiophenecarboxaldhyde (25.0 g) and triethylamine (39.7 g) in dry tetrahydrofuran (75 ml) was degasseal and stirred at room temperature under a nitrogen atmosphere. Two mole percent of bis(triphenylphosphine)palladium(II)chloride (1.8 g) followed by one mole percent of copper(I)iodide (0.25 g) was added. The mixture was degassed and stirred at room temperature under nitrogen for three days. The precipitate was filtered, and the filter cake was washed with ethyl acetate. The filtrate was evaporated, and the residue was flash chromatographed (silica, 7:3-Hexane:dichloromethane). The appropriate fractions were collected and evaporated. The residue was dried at 50° C. under vacuum for three hrs to give 35.5 g (98%) of product.

Workup

  1. additionwas added
  2. customThe mixture was degassed
  3. stirringstirred at room temperature under nitrogen for three days
  4. filtrationThe precipitate was filtered
  5. washthe filter cake was washed with ethyl acetate
  6. customThe filtrate was evaporated
  7. customchromatographed (silica, 7:3-Hexane:dichloromethane)
  8. customThe appropriate fractions were collected
  9. customevaporated
  10. customThe residue was dried at 50° C. under vacuum for three hrs

Sources & evidence

ORD record
ord-4ef069fe54d240ce94dc4f3f90519b46
Source dataset
uspto-grants-1996_01
Patent number
US05488061

Reaction notes

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