Diethylamine → HCID 15087631, compound

HRID 1722345Notes

Reaction equation

HRID 1722345 reaction equation
C(NCC)C.[C:6]([OH:12])(=[O:11])[CH2:7][CH2:8][C:9]#[CH:10].[I:13][C:14]1[S:15][CH:16]=[C:17](I)[CH:18]=1>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.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.[Pd]>[I:13][C:14]1[S:15][C:16]([C:10]#[C:9][CH2:8][CH2:7][C:6]([OH:12])=[O:11])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 224644-Pentynoic acidHCID 126435852,4-Diiodothiophene

Product 1

HCID 15087631HCID 15087631, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To 75ml of diethylamine was added with stirring 3.76g of 4-pentynoic acid, 22g of 2,4-diiodothiophene, and 300mg of tetrakis(triphenylphosphine)palladium(o). The slurry was degassed with argon and 960mg of CuI was added. The slurry was maintained under argon and allowed to stir overnight, producing a dark brown solution. Thereafter, the solvent was removed under reduced pressure and 100ml of 10% HCl was added to the residue. The residue was filtered and then extracted 3x with ethyl acetate. The combined extracts were washed 1x with water, dried over anhydrous MgSO4, filtered, and stripped. The resulting residue was flash chromatographed on a column of silica gel. Elution with a mixture of 30/70/2 parts ethyl acetate/hexane/acetic acid produced 3.5 g of the titled product as a yellow solid.

Workup

  1. customThe slurry was degassed with argon and 960mg of CuI
  2. additionwas added
  3. temperatureThe slurry was maintained under argon
  4. customproducing a dark brown solution
  5. customThereafter, the solvent was removed under reduced pressure and 100ml of 10% HCl
  6. additionwas added to the residue
  7. filtrationThe residue was filtered
  8. extractionextracted 3x with ethyl acetate
  9. washThe combined extracts were washed 1x with water
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. customchromatographed on a column of silica gel
  13. washElution
  14. additionwith a mixture of 30/70/2 parts ethyl acetate/hexane/acetic acid

Sources & evidence

ORD record
ord-eee471f44ad34ddb817b0853db686e1c
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

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