Potassium Carbonate → Ethyl-3-(6-(3-(quinolin-2-ylmethyloxy)benzyloxy)-2,3-dihydro-2-methylbenzoxazol-2-yl)propanoate

HRID 2248898Notes

Reaction equation

HRID 2248898 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1([CH3:17])[NH:11][C:10]2[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:9]=2[O:8]1)[CH3:2].Cl[CH2:20][C:21]1[CH:22]=[C:23]([CH:36]=[CH:37][CH:38]=1)[O:24][CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1([CH3:17])[NH:11][C:10]2[CH:12]=[CH:13][C:14]([O:16][CH2:20][C:21]3[CH:38]=[CH:37][CH:36]=[C:23]([O:24][CH2:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[CH:22]=3)=[CH:15][C:9]=2[O:8]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 19994713Ethyl-3-(2,3-dihydro-6-hydroxy-2-methyl-benzoxazol-2-yl)propanoate

Product 1

HCID 19994701Ethyl-3-(6-(3-(quinolin-2-ylmethyloxy)benzyloxy)-2,3-dihydro-2-methylbenzoxazol-2-yl)propanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g of ethyl-3-(2,3-dihydro-6-hydroxy-2-methyl-benzoxazol-2-yl)propanoate, 3.1 g of 2-(3-chloromethylphenoxy)methylquinoline and 1.2 g potassium carbonate are combined in 25 ml of dimethylformamide and stirred at room temperature overnight, then at 60° C. for 4 hours. The reaction mixture is diluted with ethyl acetate and this solution washed with water, dried and concentrated. The residue is chromatographed on silica gel to give ethyl-3-(6-(3-(quinolin-2-ylmethyloxy)benzyloxy)-2,3-dihydro -2-methylbenzoxazol-2-yl)propanoate which is used, without further purification, for the next step.

Workup

  1. waitat 60° C. for 4 hours
  2. washthis solution washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-fad343e8697a41a59f16bcf4aae0f90d
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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