Methyl iodide → 2-(Dimethoxymethyl)-3-(methoxymethoxy)-1-methyl-4-(trifluoromethyl)benzene

Temperature

0 °C

A n-butyllithium-1.59M n-hexane solution (40.0 ml, 64.4 mmol) was added dropwise to a solution of 1-(dimethoxymethyl)-2-(methoxymethoxy)-3-(trifluoromethyl)benzene (12.0 g, 42.9 mmol) obtained in Example (6-4) and N,N,N′,N′-tetramethylethylenediamine (9.70 ml, 64.4 mmol) in tetrahydrofuran (100 ml) at −40° C. over 5 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. After the reaction mixture was cooled to −40° C., methyl iodide (5.3 ml, 85.85 mmol) was added thereto and the mixture was further stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1) to give 2-(dimethoxymethyl)-3-(methoxymethoxy)-1-methyl-4-(trifluoromethyl)benzene as an oil (7.19 g, yield: 57%).

1. temperatureAfter the reaction mixture was cooled to −40° C.
2. stirringthe mixture was further stirred at room temperature for 30 minutes
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
5. dry with materialdried with anhydrous sodium sulfate
6. customThe residue obtained
7. customby removing the solvent under reduced pressure
8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1)

ORD record

ord-077098fdce0f4df585b76426c2ca4346

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2