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

HRID 484245

Reaction equation

HRID 484245 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-2120ede0afcf4275adf29317f53ece8c
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Linked notes

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