Water → HCID 19994693, compound

HRID 2248892Notes

Reaction equation

HRID 2248892 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[CH:35]=[CH:34][C:25]2[N:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[O:28][C:24]=2[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[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[CH:35]=[CH:34][C:25]3[N:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[O:28][C:24]=3[CH:23]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 109887374-[(Quinolin-2-yl)methoxy]phenolHCID 199947032-Benzoxazolecarboxylic acid, 6-(bromomethyl)-, ethyl ester

Product 1

HCID 19994693HCID 19994693, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

0.8 g of 4-(2-quinolinylmethyloxy)phenol, 0.89 g of ethyl 6-bromomethylbenzoxazole-2-carboxylate and 0.44 g of potassium carbonate are combined in 15 ml of dimethylformamide and heated at 70° C. for 18 hours. The mixture is poured into water and the aqueous mixture extracted with ethyl acetate. The organic solution is dried and evaporated and the resulting crude product is purified by column chromatography on silica gel to give ethyl 6-(4-(quinolin-2-ylmethyloxy)phenoxymethyl)-benzoxazole-2carboxylate.

Workup

  1. extractionthe aqueous mixture extracted with ethyl acetate
  2. customThe organic solution is dried
  3. customevaporated
  4. customthe resulting crude product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c4ffca03897b4d02857c2e7656c76aee
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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