Triethylamine → 6-(1-Dodecynyl)-2-pyridinecarboxaldehyde

HRID 235160

반응식

HRID 235160 반응식
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][CH2:20][CH3:21].C(N(CC)CC)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[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][CH2:20][CH3:21]

참가 물질

8

반응물 3

HCID 8471Triethylamine2회HCID 698211-Dodecyne3회HCID 27570096-Bromopyridine-2-carbaldehyde

생성물 1

HCID 183731096-(1-Dodecynyl)-2-pyridinecarboxaldehyde수율 29%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매2회HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
40 °C

실험 절차

To a solution of 6-bromo-2-pyridinecarboxaldehyde (3.0 g) in tetrahydrofuran (10 ml), was added sequentially bis(triphenylphosphine)palladium(II) chloride (0.178 g), copper(I)iodide (0.024 g), 1-dodecyne (3.25 ml), and triethylamine (2.12 ml). The solution was stirred at 40° C. overnight. The reaction mixture was cooled to room temperature, charged again with bis(triphenylphosphine)palladium (II) chloride (0.024 g), copper (I) iodide (0.024 g), and triethylamine (2.12 ml), and 1-dodecyne (3.25 ml), and tetrahydrofuran (5.0 ml), and heated at 40° C. for 5 hrs. The reaction mixture was again cooled and recharged as above, and heated at 40° C. for 24 hrs. The cooled mixture was concentrated, taken up in ethyl acetate (100 ml), washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was taken up in ethyl acetate (100 ml) and filtered. The filtrate was combined with material from a similar reaction run 1.43 g of the carboxaldehyde and proportionate amounts of the catalysts, 1-dodecyne, and solvent. The filtrate was concentrated. The residue was purified by flash chromatography using 1.5% ethyl acetate/hexane followed by 1% ethyl acetate/hexane as eluents. The appropriate fractions were collected and concentrated to yield 2.24 g (29%) of product, as an oil.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureheated at 40° C. for 5 hrs
  3. temperatureThe reaction mixture was again cooled
  4. temperatureheated at 40° C. for 24 hrs
  5. concentrationThe cooled mixture was concentrated
  6. washwashed with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. filtrationfiltered
  11. customThe filtrate was combined with material from a similar reaction
  12. concentrationThe filtrate was concentrated
  13. customThe residue was purified by flash chromatography
  14. customThe appropriate fractions were collected
  15. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8531f43721384aa69de8006ccfdf860e
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597838

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