Potassium Carbonate → HCID 68453947, compound

HRID 2355113Notes

Reaction equation

HRID 2355113 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:29]=[CH:28][CH:27]=[CH:26][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([OH:25])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:31][C:32]#[N:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:5]1[O:6][C:7]2[CH:29]=[CH:28][CH:27]=[CH:26][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([O:25][CH2:31][C:32]#[N:33])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68452159HCID 68452159, compound

Product 1

HCID 68453947HCID 68453947, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthol (1.29 g, 3.37 mmol), prepared in the previous step, bromoacetonitrile (282 μL, 4.05 mmol) and of potassium carbonate (2.33g, 16.8 mmol) in 100 mL of DMF was stir under nitrogen overnight at room temperature. The reaction was diluted with ethyl acetate, extracted three times with water, dried (MgSO4), filtered and the solvent was removed under reduced pressure to give ({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (1.12 g, 79%) as a white solid, mp 127-127° C. Elemental Analysis for C27H22N2O3 Calc'd: C, 76.76; H, 5.25; N, 6.63. Found: C, 76.53; H, 5.22; N, 6.59.

Workup

  1. extractionextracted three times with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-59f6c630769f46808d70fb988dd1705c
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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