Methyl iodide → 5-[2-(2-Chloro-4-methoxy-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one

HRID 2386855Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:20][C:19](=[O:21])[N:18]([CH3:22])[C:17]=2[CH:23]=1)=[O:12].[H-].[Na+].[CH3:26]I>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:26])[C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:20][C:19](=[O:21])[N:18]([CH3:22])[C:17]=2[CH:23]=1)=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

5-[2-(2-Chloro-4-methoxy-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one (2.45 g) was dissolved in DMF (60 mL). The mixture was cooled to 0° C. To this solution was added sodium hydride (55% in mineral oil, 403 mg) over a period of 10 minutes. The mixture was stirred for 10 minutes at 0° C. and then for 1 hour at r.t. The mixture was cooled to 0° C. and methyl iodide (0.49 mL) was added dropwise over a period of 10 minutes. Stirring was continued for 1.5 hours at r.t. The reaction mixture was poured into ice/water and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a light brown foam (1.99 g, 76%). MS (m/e)=346.1 [M+H+].

Workup

waitfor 1 hour at r.t
temperatureThe mixture was cooled to 0° C.
stirringStirring
waitwas continued for 1.5 hours at r.t
extractionextracted three times with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record: ord-5bc51352be454085b33720b5c9478359
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268820B2

Reaction notes

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