Triethylamine → 6-(1-Undecynyl)pyridine-2-carboxaldehyde

HRID 977540ノート

反応式

HRID 977540 の反応式
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].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:10]([C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1)#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 752491-UndecyneHCID 27570096-Bromopyridine-2-carbaldehyde

生成物 1

HCID 153806466-(1-Undecynyl)pyridine-2-carboxaldehyde収率 84.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 6-bromopyridine-2-caboxaldehyde (15.0 g), 1-undecyne (12.9 g), triethylamine (24.5 g), bis(triphenylphosphine)palladium(II)chloride (1.1 g, 2%), and copper(I)iodide (0.15g, 1%) in dry tetrahydrofuran (60 ml) was heated under nitorgen at 55° C. for 10 hrs. The reaction mixture was filtered, the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, and the solution was washed with half-saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed on silica gel, eluting with 0%-2%-ethyl acetate:hexane. The appropriate fractions were collected and evaporated to yield 17.5 g (84.0%) of product.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with ethyl acetate
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with half-saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customchromatographed on silica gel
  10. washeluting with 0%-2%-ethyl acetate
  11. customThe appropriate fractions were collected
  12. customevaporated

出典と根拠

ORDレコード
ord-e918484e906440249990daf664e26c8e
出典データセット
uspto-grants-1997_03
特許番号
US05614631

反応ノート

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