1-Indanone → 6-[(2-Naphthyl)methoxy]-2-methyl-indanone

HRID 37698

反応式

HRID 37698 の反応式
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11]([O-:14])([O-])=O.[K+].[K+].[CH2:17]1OCCOCCOCCOCCOCCOC1.BrC[C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=1>C(#N)C>[CH:38]1[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:45]=[CH:46][C:37]=1[CH2:11][O:14][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH:2]([CH3:17])[C:1]2=[O:10])=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 67351-IndanoneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 703202-Bromomethylnaphthalene

生成物 1

HCID 199357556-[(2-Naphthyl)methoxy]-2-methyl-indanone収率 697.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

A mixture of the indanone (14 g, 86.4 mmole) prepared as described in Example 1, Step D, anhydrous K2CO3 (11.24 g, 81.4 mmole), 18-crown-6 (2.29 g, 6.4 mmole) and 2-bromomethylnaphthalene (11.6 g, 95 mmole) in acetonitrile (275 mL) is heated under nitrogen for 24 hours (in an oil bath set at 70° C.). The acetonitrile is evaporated and the residue is dissolved in water, extracted with ethyl acetate, dried (MgSO4) and evaporated to dryness. The crude product (tan solid) is flash chromatographed (on silica Merck-60, preabsorbed in CH2Cl2, eluted with 8:2 hexane-ethyl acetate) to provide the title compound as a white solid (13.49 g, 52% ).

後処理

  1. customprepared
  2. customThe acetonitrile is evaporated
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customchromatographed
  8. custom(on silica Merck-60, preabsorbed in CH2Cl2, eluted with 8:2 hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-46a992045757439585144887b9465636
出典データセット
uspto-grants-1995_05
特許番号
US05420289

関連ノート

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