Sulfuric Acid → 2-{2-Methoxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl ester

HRID 1181138Notes

Reaction equation

HRID 1181138 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][OH:31])([CH3:7])[CH3:6])[CH3:2].[CH3:33]I.[H-].[Na+].S(=O)(=O)(O)O>[Cl-].[Na+].O.CCOC(C)=O.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:32])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][O:31][CH3:33])([CH3:7])[CH3:6])[CH3:2]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 235900112-{2-Hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl ester

Product 1

HCID 589790592-{2-Methoxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl esterYield 51%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 15 mL round bottomed flask under a nitrogen atmosphere were charged with 2-{2-hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl ester (0.075 g, 0.17 mmol), anhydrous DMF (1 mL), and then methyl iodide (0.16 mL, 1.7 mmol). The solution was cooled in an ice bath and was treated with NaH (0.014 g, 0.34 mmol, 60% oil dispersion). The mixture was stirred for 2 h, poured into EtOAc (6 mL) and brine (10 mL), and acidified using dilute sulfuric acid. The organic layer was separated, dried (Na2SO4), and concentrated to an oil. The crude product was purified using radial chromatography (EtOAc:Hex 15:85) to give a colorless oil (0.039 g, 51%). MS (ES) m/e 454 (M+1).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-0dce8d3d0fc8497685aec33867600733
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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