Diethylamine → HCID 15087631、化合物

HRID 1073576ノート

反応式

HRID 1073576 の反応式
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>>[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

参加物

4

反応物 3

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

生成物 1

HCID 15087631HCID 15087631、化合物収率 29.8%

実験手順

To 75 ml of diethylamine was added with stirring 3.76 g of 4-pentynoic acid, 22 g of 2,4-diiodothiophene, and 300 mg of tetrakis-(triphenylphosphine)palladium(o). The slurry was degassed with argon and 960 mg 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 100 ml of 10% HCl was added to the residue. The residue was filtered and then extracted 3 x with ethyl acetate. The combined extracts were washed 1 x 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.

後処理

  1. customThe slurry was degassed with argon and 960 mg 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 100 ml of 10% HCl
  6. additionwas added to the residue
  7. filtrationThe residue was filtered
  8. extractionextracted 3 x with ethyl acetate
  9. washThe combined extracts were washed 1 x 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

出典と根拠

ORDレコード
ord-9897c614ae764c99ace1cce82d34d448
出典データセット
uspto-grants-1990_11
特許番号
US04970229

反応ノート

読み込み中…