Potassium Carbonate → HCID 19994678, compound

HRID 2248888Notes

Reaction equation

HRID 2248888 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.Br[CH2:21][C:22]1[C:30]2[O:29][C:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[N:27][C:26]=2[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OC(=O)C)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:21][C:22]2[C:30]3[O:29][C:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[N:27][C:26]=3[CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 109887374-[(Quinolin-2-yl)methoxy]phenolHCID 19994739HCID 19994739, compound

Product 1

HCID 19994678HCID 19994678, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.8 g of 4-(2-quinolinylmethyloxy)phenol, 1.98 g of ethyl 7-bromomethylbenzoxazole-2-carboxylate and 1.0 g of potassium carbonate are combined in 100 ml of acetone and refluxed for 18 hours. The mixture is cooled, diluted with ethylacetate and filtered. The filtrate is concentrated and the crude product purified by flash chromatography on silica gel in 5% ethanol in chloroform/hexane (1:1) to give ethyl 7-(4-(quinolin-2-ylmethoxy)phenoxymethyl)benzoxazole-2-carboxylate.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customthe crude product purified by flash chromatography on silica gel in 5% ethanol in chloroform/hexane (1:1)

Sources & evidence

ORD record
ord-866eb50ebae348cbb196c30c08be7bff
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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