4-Bromoanisole → 2-Methoxy-6-(4-methoxyphenyl)-8-methylquinoline

HRID 568351ノート

反応式

HRID 568351 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.Br[C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([CH3:26])[CH:25]=1)[N:22]=[C:21]([O:27][CH3:28])[CH:20]=[CH:19]2>CCCCCC.C1COCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][O:27][C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[C:24]([CH3:26])[CH:25]=[C:16]([C:7]3[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=3)[CH:17]=2)[N:22]=1

参加物

8

反応物 3

HCID 77304-BromoanisoleHCID 14220967HCID 14220967、化合物HCID 178418339Butyllithium

生成物 1

HCID 201504532-Methoxy-6-(4-methoxyphenyl)-8-methylquinoline

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

n-Butyllithium (33.3 cm3 of a 1.5M solution in n-hexane) was added dropwise at -70° to a stirred solution of 4-bromoanisole (6.26 cm3) in THF (70 cm3) under nitrogen. After ten minutes, a solution of anhydrous zinc chloride (6.814 g) in THF (50 cm3) was added and the mixture was allowed to warm to room temperature over 0.5 hour. A mixture of 6-bromo-2-methoxy-8-methylquinoline (12.8 g) and tetrakis(triphenylphosphine)palladium (0) (0.5 g) was added and the mixture heated under reflux for 2 hours. Volatile material was removed in vacuo and the residue was partitioned between chloroform (150 cm3) and a solution of ethylenediaminetetraacetic acid (40 g) in water (250 cm3). The organic layer was dried (MgSO4) and evaporated to afford an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with hexane:ethyl acetate, 19:1. Combination and evaporation of the appropriate fractions afforded the title compound (5.49 g). A small portion of this was recrystallised from methanol and had m.p. of 104°-106° and the following analysis:

後処理

  1. waitAfter ten minutes
  2. additionwas added
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 2 hours
  5. customVolatile material was removed in vacuo
  6. customthe residue was partitioned between chloroform (150 cm3)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated
  9. customto afford an oil which
  10. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  11. washeluting with hexane
  12. customCombination and evaporation of the appropriate fractions

出典と根拠

ORDレコード
ord-32b1d0fb7a894ede8724d19645242259
出典データセット
uspto-grants-1988_03
特許番号
US04728654

反応ノート

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