Dimethyl Sulfoxide → 4-(Propynyloxy)pyridine

HRID 27041

반응식

HRID 27041 반응식
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.CS(C)=O.[CH2:12](Cl)[C:13]#[CH:14]>O.C(=O)([O-])[O-].[Ag+2]>[C:12]([O:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)#[C:13][CH3:14]

참가 물질

6

반응물 3

HCID 679Dimethyl SulfoxideHCID 122213-Chloro-1-propyneHCID 178418642HCID 178418642, 화합물

생성물 1

HCID 233434924-(Propynyloxy)pyridine수율 3.6%

시약·촉매·용매 2

HCID 178418647HCID 178418647, 화합물촉매HCID 962Water용매

실험 절차

To a solution of 20.0 g (0.21 mole) 4-hydroxypyridine and 200 ml dimethyl sulfoxide was added 102 g (0.1 mole) silver carbonate. Propargyl chloride (22.5 g, 0.3 mole) was added to this suspension and the mixture heated at 50° for 6 hrs. After cooling to room temperature, the reaction mixture was diluted with water and extracted two times with ether. The combined ether extract was dried, filtered and concentrated as before to give 1.0 g of 4-(propynyloxy)pyridine. The product was 95% pure by vpc. The nmr and ir were compatible with the structure.

후처리

  1. temperaturethe mixture heated at 50° for 6 hrs
  2. extractionextracted two times with ether
  3. extractionThe combined ether extract
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated as before

출처 및 근거

ORD 기록
ord-6a8c1777713940babd8f296f2d89bc27
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220577

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