Sodium Iodide → HCID 67279236, compound

HRID 1694654Notes

Reaction equation

HRID 1694654 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl[CH2:15][C:16]1[N:17]=[C:18]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)[O:19][CH:20]=1.[I-].[Na+]>CN(C)C=O.O>[F:27][C:25]1[CH:24]=[C:23]([C:28]([F:29])([F:30])[F:31])[CH:22]=[C:21]([C:18]2[O:19][CH:20]=[C:16]([CH2:15][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[N:17]=2)[CH:26]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 67279270HCID 67279270, compound

Product 1

HCID 67279236HCID 67279236, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

In a 50 mL round bottomed flask was placed diethyl malonate (3.72 g, 23.25 mmol, 5 equiv.) and N,N-dimethylformamide (10 mL). To the solution was added sodium hydride (60% suspension in mineral oil, 744.0 mg, 18.6 mmol, 4.0 equiv.) at room temperature portionwise over 10 minutes. After stirring for 30 minutes a solution of 4-(chloromethyl)-2-[5-fluoro-3-(trifluoromethyl)phenyl]-1,3-oxazole (1.30 g, 4.65 mmol) in N,N-dimethylformamide (10 mL) was added at 0° C. over 15 minutes, and the reaction mixture allowed to warm up to ambient temperature. To the mixture was added sodium iodide (697.0 mg, 4.65 mmol, 1 equiv) at room temperature. The reaction mixture was stirred at the same temperature for 2 hours. Water was then added to the reaction mixture (30 mL) and the whole was extracted with ethyl acetate (30 mL×3). The organic layers were combined, washed with brine (30 mL) and dried with sodium sulfate. After removal of the solvent under reduced pressure the crude mixture was purified by a silica-gel column chromatography (SiO2=80 g, hexane:EtOAc=7:1) repeatedly. The desired product, diethyl 2-({2-[5-fluoro-3-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methyl)propane-1,3-dioate, was obtained as colorless powder (1.75 g).

Workup

  1. customIn a 50 mL round bottomed flask was placed
  2. additionwas added at 0° C. over 15 minutes
  3. extractionthe whole was extracted with ethyl acetate (30 mL×3)
  4. washwashed with brine (30 mL)
  5. dry with materialdried with sodium sulfate
  6. customAfter removal of the solvent under reduced pressure the crude mixture
  7. customwas purified by a silica-gel column chromatography (SiO2=80 g, hexane:EtOAc=7:1) repeatedly

Sources & evidence

ORD record
ord-9087ed908bcb4624aacb9a990b8b6490
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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