Potassium Carbonate → HCID 18930054, compound

HRID 1598629Notes

Reaction equation

HRID 1598629 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[CH:13]1([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:13]1([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:2][C:3]3[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=3[C:5]([O:7][CH3:8])=[O:6])=[CH:26][CH:27]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2211374-(1-Indanyl)PhenolHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 18930054HCID 18930054, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-(bromomethyl)benzoate (10.00 g, 43.7 mmol), 4-(1-indanyl)phenol (11.47 g, 54.5 mmol), and potassium carbonate (13.27 g, 96.0 mmol) in DMF was heated at 60° C. for 4h, then was allowed to stir at room temperature for 3d. The resulting reaction mixture was partitioned between ether and water, then the organic phase was dried over magnesium sulfate, concentrated, and purified by chromatography over silica gel eluted with 4% ethyl acetate in hexanes to afford 14.8 g of methyl 2-[4-(1-indanyl)phenoxymethyl]benzoate as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. customwas partitioned between ether and water
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by chromatography over silica gel
  6. washeluted with 4% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-07ab7bc170954a77800b30c3b7e109d0
Source dataset
uspto-grants-1998_04
Patent number
US05739140

Reaction notes

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