Potassium Carbonate → 6-(2-Quinolinylmethoxy)-2-methyl-1-indanone

HRID 484242

反応式

HRID 484242 の反応式
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH3:12])[C:8]2=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Cl[CH2:38][C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:40]=1>CCCCCC.C(#N)C>[N:40]1[C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:47]=[CH:48][C:39]=1[CH2:38][O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH3:12])[C:8]2=[O:11])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 2855718-Crown-6HCID 2343386-Hydroxy-2-methyl-2,3-dihydro-1h-inden-1-one

生成物 1

HCID 199357276-(2-Quinolinylmethoxy)-2-methyl-1-indanone収率 84.8%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8058Hexane溶媒

実験手順

A mixture of the phenol (15.16 g, 93.58 mmole) of Step D, powdered anhydrous potassium carbonate (12.93 g, 93.6 mmole), 18-crown-6 (2.47 g, 9.36 mmole) and dry acetonitrile (200 mL) is stirred at room temperature under a nitrogen for 15 minutes. 2-Chloromethylquinoline (free base, freshly prepared from 18.29 g or 102.96 mmole of the hydrochloride salt) is added in one portion and the mixture is placed in an oil bath heated at 65° C. for 11 hours (TLC, dichloromethanemethanol 9:1, UV). The solvent is removed in vacuo and the residue is partitioned between ethyl acetate and water. The organic phase is washed with brine, dried (MgSO4) and evaporated to yield an oil which solidifies upon trituration with hexane (ca. 31 g). The crude product is purified by flash chromatography (on silica Merck-60, absorbed in methylene chloride, eluted with CH2Cl2 -ethyl acetate 90:10 and 85:15) to provide 5.95 g of slightly impure material together with 24.55 g of the pure title compound (pale yellow solid, 84.8%).

後処理

  1. additionis added in one portion
  2. customthe mixture is placed in an oil bath
  3. temperatureheated at 65° C. for 11 hours (TLC, dichloromethanemethanol 9:1, UV)
  4. customThe solvent is removed in vacuo
  5. customthe residue is partitioned between ethyl acetate and water
  6. washThe organic phase is washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto yield an oil which
  10. customThe crude product is purified by flash chromatography (on silica Merck-60, absorbed in methylene chloride, eluted with CH2Cl2 -ethyl acetate 90:10 and 85:15)

出典と根拠

ORDレコード
ord-e8a330f6c75b4e9c96984224ce086cfd
出典データセット
uspto-grants-1993_07
特許番号
US05229516

関連ノート

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