Methyl iodide → HCID 71044243, compound

HRID 915195Notes

Reaction equation

HRID 915195 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]([CH:32]([CH3:34])[CH3:33])=[C:12]([CH2:14][CH2:15][C:16]([C:18]2[CH:30]=[CH:29][C:21]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:20]([CH3:31])[CH:19]=2)=[O:17])[N:13]=1.[H-].[Na+].[CH3:37]I>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]([CH:32]([CH3:33])[CH3:34])=[C:12]([CH2:14][CH:15]([CH3:37])[C:16]([C:18]2[CH:30]=[CH:29][C:21]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:20]([CH3:31])[CH:19]=2)=[O:17])[N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 86596912HCID 86596912, compound

Product 1

HCID 71044243HCID 71044243, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [4-[3-[2-(2,4-dichlorophenyl)-5-isopropyl-4-oxazolyl]propionyl]-2-methylphenoxy]acetate (450 mg, 0.89 mmol) was dissolved in dry THF (4 mL). Sodium hydride (40 mg, 1.00 mmol) was gradually added to the solution. The mixture was stirred for 30 minutes at room temperature. Methyl iodide (0.07 mL, 1.12 mmol) was dropwise added to the mixture. The resulting mixture was stirred for 27 hours at room temperature. Sodium hydride (10 mg, 0.25 mmol) and methyl iodide (0.02 mL, 0.32 mmol) were further added to the mixture. The resulting mixture was stirred for 19 hours 30 minutes at room temperature. The solvent was removed under reduced pressure. Ethyl acetate (5 mL) was added to the residue. The residue was washed with a saturated saline (2 mL), and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel with ethyl acetate/hexane (1/9) to give the desired compound (218 mg) as colorless oil (purity 97%, yield 29%).

Workup

  1. stirringThe resulting mixture was stirred for 27 hours at room temperature
  2. stirringThe resulting mixture was stirred for 19 hours 30 minutes at room temperature
  3. customThe solvent was removed under reduced pressure
  4. additionEthyl acetate (5 mL) was added to the residue
  5. washThe residue was washed with a saturated saline (2 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel with ethyl acetate/hexane (1/9)

Sources & evidence

ORD record
ord-eb984db4c62949e49dcc696905936446
Source dataset
uspto-grants-2007_09
Patent number
US07265137B2

Reaction notes

Loading…