Pyridine → HCID 86741244、化合物

HRID 980926

反応式

HRID 980926 の反応式
[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]

参加物

8

反応物 4

HCID 1049PyridineHCID 1140TolueneHCID 22321436HCID 22321436、化合物HCID 542654372,6-Dichloro-3-nitrophenylacetic acid

生成物 1

HCID 86741244HCID 86741244、化合物収率 61.7%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8078Cyclohexane溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b8f6548b8bfe4fb1a9f5d3fc2406b2cd
出典データセット
uspto-grants-1987_01
特許番号
US04639541

関連ノート

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