Water → HCID 22934068, compound

HRID 1269835Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH3:12].[CH2:20]([Li])CCC.CI.O>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[C:5]([NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-[3-methoxy-4-(methoxymethoxy)phenyl]-2,2-dimethylpropanamide (500 mg, 1.87 mmol) in tetrahydrofuran (10 ml) was added dropwise 1.59M-n-butyllithium (2.94 ml, 4.68 mmol) at −15° C., and the resulting mixture was slowly warmed up to 0° C. After 2 hours, a solution of methyl iodide (0.175 ml, 2.81 mmol) in tetrahydrofuran (0.5 ml) was added dropwise thereto. After 1 hour, the resulting mixture was warmed up to room temperature. After 14 hours, the reaction solution was poured into water (50 ml) and extracted with ethyl acetate (30 ml×3), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain N-[3-methoxy-4-(methoxymethoxy)-2-methylphenyl]-2,2-dimethylpropanamide (424 mg, 81%).

Workup

waitAfter 1 hour
temperaturethe resulting mixture was warmed up to room temperature
waitAfter 14 hours
extractionextracted with ethyl acetate (30 ml×3)
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customThe organic layer dried
concentrationwas concentrated under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-7cda0fcd33fa4275b76c0be68ca034c0
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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