8-Methoxyquinoline → 8-Methoxy-2-(2-methoxyphenyl)quinoline

HRID 1893143

反応式

HRID 1893143 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.[Li][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21].C(OCC)(=O)C.CCCCCC>C(OCC)C.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH:9]=[CH:8]2

参加物

6

反応物 3

HCID 703108-MethoxyquinolineHCID 21226206Ethyl acetate hexaneHCID 178506687HCID 178506687、化合物

生成物 1

HCID 672565848-Methoxy-2-(2-methoxyphenyl)quinoline

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 8-methoxyquinoline (5.54 g, 34.8 mmol, 1.0 eq) in 55 ml diethyl ether was slowly dropped (within about 30 min) into a solution of o-lithioanisole (4.37 g, 38.4 mmol, 1.1 eq) in 55 ml diethyl ether (each 55 mL). A yellow green fluorescing solution was formed. At the conclusion of the addition, stirring was continued at room temperature for a further 2 hours, after which no more educt could be detected by thin layer chromatography. During the reaction, the color of the reaction mixture changed from fluorescent yellow to green to green-brown. The reaction mixture was worked up by adding it to ice and subsequent extraction with diethyl ether (3×40 ml). The combined organic phases (yellow) were dried over MgSO4 and the solvent was removed in a rotary evaporator. The residue was dissolved in 200 ml dichloromethane and stirred with ca. 40 equivalents of activated manganese dioxide (Merck) until the thin layer chromatographic control (ethyl acetate/hexane=4/6) showed that all of the crude product had reacted. The manganese dioxide was filtered off and the solvent removed in the rotary evaporator. The product was dried under vacuum.

後処理

  1. customA yellow green fluorescing solution was formed
  2. additionAt the conclusion of the addition
  3. customDuring the reaction
  4. additionby adding it
  5. extractionto ice and subsequent extraction with diethyl ether (3×40 ml)
  6. dry with materialThe combined organic phases (yellow) were dried over MgSO4
  7. customthe solvent was removed in a rotary evaporator
  8. dissolutionThe residue was dissolved in 200 ml dichloromethane
  9. customhad reacted
  10. filtrationThe manganese dioxide was filtered off
  11. customthe solvent removed in the rotary evaporator
  12. customThe product was dried under vacuum

出典と根拠

ORDレコード
ord-14b7c19316fd4cf2abc8f9176a91023f
出典データセット
uspto-grants-2013_08
特許番号
US08513177B2

関連ノート

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