Potassium Carbonate → 2-Methyl-5-(2-quinolinylmethoxy)-1H-indene-3-acetic acid methyl ester

HRID 484263Notes

Reaction equation

HRID 484263 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[CH2:7][C:6]=1[CH3:15].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Cl[CH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[N:44]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:42][C:43]3[CH:52]=[CH:51][C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[N:44]=3)[CH:12]=2)[CH2:7][C:6]=1[CH3:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 2855718-Crown-6HCID 224569872-methyl-5-hydroxy-1H-indene-3-acetic acid methyl ester

Product 1

HCID 152880532-Methyl-5-(2-quinolinylmethoxy)-1H-indene-3-acetic acid methyl esterYield 79.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methyl-5-hydroxy-1H-indene-3-acetic acid methyl ester (1.8 g, 8.25 mmol), powdered anhydrous potassium carbonate (1.13 g, 8.25 mmol) and 18-crown-6 (0.219 g) in acetonitrile (21 mL) is stirred at room temperature for 15 minutes. 2-(Chloromethyl)quinoline (1.6 g, 9.08 mmol) is then added and the mixture is stirred for 15 hours at 65° C. After the solvent is removed, the residue is partitioned between water and ethyl acetate. The organic phase is dried over MgSO4 and evaporated. The crude product is purified by flash chromatography (eluant: methylene chloride-ethyl acetate) to afford 2.35 g (79%) of the desired product.

Workup

  1. stirringthe mixture is stirred for 15 hours at 65° C
  2. customAfter the solvent is removed
  3. customthe residue is partitioned between water and ethyl acetate
  4. dry with materialThe organic phase is dried over MgSO4
  5. customevaporated
  6. customThe crude product is purified by flash chromatography (eluant: methylene chloride-ethyl acetate)

Sources & evidence

ORD record
ord-370dcb37d0f34aca9bcafddcfb00c556
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Reaction notes

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