3-Pyridinemethanol → 3-(2-Propynyloxymethyl)pyridine

HRID 27040

반응식

HRID 27040 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].[CH2:11](Cl)[C:12]#[CH:13]>CN(C)C=O>[CH2:13]([O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:12]#[CH:11]

참가 물질

5

반응물 3

HCID 75103-PyridinemethanolHCID 122213-Chloro-1-propyneHCID 24758Sodium hydride

생성물 1

HCID 139264073-(2-Propynyloxymethyl)pyridine수율 45.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

While maintaining the reaction mixture at 5°-10° C., 3-pyridylcarbinol (50.0 g., 0.45 mol) was slowly added to a mixture of sodium hydride (24.0 g of a 50% suspension in mineral oil, 0.5 mol) in 250 ml dry N,N-dimethylformamide. Propargyl chloride (37.0 g, 0.5 mole) was then slowly added to this mixture at 15° C. Following the addition, the reaction mixture was warmed to 35° and maintained for 15 mins at this temperature. The reaction was then cooled to 15°-20°, carefully quenched by dropwise addition of water and extracted with ether. The combined ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 45 g crude product. Distillation gave 30.0 g of 3-(2-propynyloxymethyl)pyridine. Yield 44% theory; b.p. 95° C. (0.9 mm).

후처리

  1. temperatureWhile maintaining the reaction mixture at 5°-10° C.
  2. additionthe addition
  3. temperaturethe reaction mixture was warmed to 35°
  4. temperaturemaintained for 15 mins at this temperature
  5. temperatureThe reaction was then cooled to 15°-20°
  6. customcarefully quenched by dropwise addition of water
  7. extractionextracted with ether
  8. dry with materialThe combined ether extracts were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto give 45 g crude product
  12. distillationDistillation

출처 및 근거

ORD 기록
ord-c848ad90b5f249fcaa1746e449176934
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220577

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