Pyridine → HCID 86741244, 화합물

HRID 980926

반응식

HRID 980926 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([OH:15])=[O:14].[I:16][CH2:17][C:18]#[C:19]O.N1C=CC=CC=1.C1(C)C=CC=CC=1>C1CCCCC1.S(Cl)(Cl)=O.C(OCC)C>[I:16][CH:17]([O:14][C:13](=[O:15])[CH2:12][C:3]1[C:4]([Cl:11])=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[Cl:1])[C:18]#[CH:19]

참가 물질

8

반응물 4

HCID 1049PyridineHCID 1140TolueneHCID 22321436HCID 22321436, 화합물HCID 542654372,6-Dichloro-3-nitrophenylacetic acid

생성물 1

HCID 86741244HCID 86741244, 화합물수율 61.7%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8078Cyclohexane용매HCID 24386Thionyl Chloride용매

반응 조건

온도
30 °C

실험 절차

15 g (0.06 moles) of 2,6-dichloro-3-nitrophenylacetic acid were suspended in 30 ml of cyclohexane and 20 ml of thionyl chloride. The whole was refluxed until the evolution of gas was complete. Subsequently, excess thionyl chloride and cyclohexane were distilled off. The resulting acid chloride was dissolved in 50 ml of absolute toluene and, while stirring, at a temperature of 30° C., added dropwise to a mixture of 11 g (0.06 moles) of 3-iodopropynol, 4.75 g of pyridine and 50 g of toluene. After 1 hour the reaction mixture was taken up in diethyl ether and the ethereal solution was extracted with 1N hydrochloric acid and then with saturated sodium bicarbonate solution. Finally, the organic phase was washed with water, dried with sodium sulfate and concentrated by evaporation. The crude product (22.7 g) was further purified by chromatography over silica gel. 15.5 g (0.037 moles) of 2,6-dichloro-3-nitrophenylacetic acid iodopropargyl ester corresponding to 63% of the theoretical yield, were obtained. Melting range 97°-99° C.

후처리

  1. temperatureThe whole was refluxed until the evolution of gas
  2. distillationSubsequently, excess thionyl chloride and cyclohexane were distilled off
  3. dissolutionThe resulting acid chloride was dissolved in 50 ml of absolute toluene
  4. extractionthe ethereal solution was extracted with 1N hydrochloric acid
  5. washFinally, the organic phase was washed with water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe crude product (22.7 g) was further purified by chromatography over silica gel

출처 및 근거

ORD 기록
ord-b8f6548b8bfe4fb1a9f5d3fc2406b2cd
출처 데이터셋
uspto-grants-1987_01
특허 번호
US04639541

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