1-Octyne → HCID 20147157, compound

HRID 569489Notes

Reaction equation

HRID 569489 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[CH:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(N(CC)CC)C>[C:9]([C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1)#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 123701-OctyneHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 20147157HCID 20147157, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
105 °C

Procedure

5-Bromo-2-thiophenecarboxaldehyde (8.5 g, 0.05 mole) was combined with 1-octyne (11.0 g, 0.1 mole) and triethylamine (200 ml). The mixture was degassed under argon and cuprous iodide (950 mg, 10 mole %) and tetrakis (triphenylphosphine) palladium (1.75 g, 5 mole %) were added. The mixture was heated at 105° C. for twenty hours under argon and cooled. The triethylamine was evaporated and the residue purified by chromatography on silica eluting with hexane/chloroform (3:1) to yield the title compound 8.6 g (83.7%) as a yellow oil. mp 130° C., νmax (film) 3320, 2225, 1675, 1050, 805, 780, 675; δ(CDCl3) 0.87(3H, t, J=6 Hz), 1.33(8H, m), 2.33(2H, t, J=6 Hz), 7.13(1H, d, J=6 Hz), 7.65(1H, d, J=6 Hz), 9.87(1H, s).

Workup

  1. customThe mixture was degassed under argon
  2. additioncuprous iodide (950 mg, 10 mole %) and tetrakis (triphenylphosphine) palladium (1.75 g, 5 mole %) were added
  3. temperaturecooled
  4. customThe triethylamine was evaporated
  5. customthe residue purified by chromatography on silica eluting with hexane/chloroform (3:1)

Sources & evidence

ORD record
ord-1a55d9ef7a554df893de3b38125b81d0
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Reaction notes

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