Dimethylformamide → HCID 86661605, compound

HRID 1182821Notes

Reaction equation

HRID 1182821 reaction equation
CN(C)[CH:3]=[O:4].[Br:6][C:7]1[O:11][C:10]([C:12]2[O:13][C:14]([CH3:19])=[C:15]([CH2:17]Br)[N:16]=2)=[CH:9][CH:8]=1.[C:20]([O-])(=[O:22])C.[Na+]>O>[Br:6][C:7]1[O:11][C:10]([C:12]2[O:13][C:14]([CH3:19])=[C:15]([CH2:17][C:20]([O:4][CH3:3])=[O:22])[N:16]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 66706091HCID 66706091, compound

Product 1

HCID 86661605HCID 86661605, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The N,N-dimethylformamide (1.5 mL) solution of 2-(5-bromofuran-2-yl)-4-(bromomethyl)-5-methyloxazole (32 mg, 0.1 mmol) and sodium acetate (12 g, 0.15 mmol) was stirred at 80° C. overnight. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain methyl {2-(5-bromofuran-2-yl)-5-methyloxazol-4-yl}acetate as a yellow oil (25 mg, 83%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ddc0811045994025ae5a609d9aca53b8
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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