N,N,N',N'-Tetramethylethylenediamine → HCID 58223482, compound

To a tetrahydrofuran (45 ml) solution of 1-cyclopropyl-3,5-dimethoxybenzene (1.59 g, 8.92 mmol) was added N,N,N,N-tetramethylethylenediamine (2.01 ml, 13.4 mmol) at room temperature and 2.77M n-butyllithium (4.83 ml, 13.4 mmol) was added dropwise at −78° C., and the mixture was stirred at room temperature for two hours. The temperature was returned to −78° C. again, trimethyl borate (1.49 ml, 13.4 mmol) was added dropwise and warmed to room temperature, and the mixture was stirred for 13 hours. After the reaction was completed, a saturated aqueous solution of ammonium chloride was added to the reaction mixture while cooling on ice, which was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1) to obtain the title compound (1.36 g, 6.12 mmol).

1. customwas returned to −78° C.
2. temperaturewarmed to room temperature
3. stirringthe mixture was stirred for 13 hours
4. temperaturewhile cooling on ice, which
5. extractionwas extracted with ethyl acetate
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1)

ORD record

ord-42f97df01fb3411c9a6f25246a0ef91e

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530504B2