4,4-Dimethyl-2-(2-methoxyphenyl)oxazoline → 2-(2-Dodecylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

To freshly prepared dodecylmagnesium bromide (from 30.13 mmol of dodecyl bromide and 26.20 mmol of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmol) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil.

1. temperatureThe solution was cooled in an ice water bath
2. customquenched with aqueous ammonium chloride (100 ml)
3. extractionThe reaction product was extracted into diethyl ether (100 ml)
4. washthe organic phase was washed with saturated sodium chloride solution (50 ml)
5. dry with materialdried over anhydrous magnesium sulfate
6. customEvaporation of the organic phase
7. customafforded a colorless oil which
8. customwas purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant

ORD record

ord-16e3aca1803343b4a275ce48e553e22b

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05135938