Dimethylformamide → HCID 23155341, compound

Temperature

0 °C

At −78° C., a hexane solution of n-butyl lithium (100 mmol/64 ml) was added dropwise to a THF (200 ml) solution including 15.0 g (83 mmol) of the above-mentioned compound A2 and 15 ml (100 mmol) of tetramethylethylenediamine (TMEDA). After 30 min, the solution was heated to 0° C., stirred for 1 hour, and again cooled to −78° C. Dimethylformamide (DMF) (15.9 ml) was then added dropwise. After the reaction solution was slowly heated to room temperature, the reaction solution was poured into a saturated aqueous solution of ammonium chloride. The aqueous phase was extracted with ether. The organic phases were combined and washed with water and a saturated sodium chloride solution in that order and then dried using anhydrous sodium sulfate. After removing the drying agent by filtering, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography to obtain 3-isopropyl-2-methoxy methoxybenzaldehyde (12.9 g, 74% yield, reference symbol A3 in FIG. 1).

1. temperatureagain cooled to −78° C
2. temperatureAfter the reaction solution was slowly heated to room temperature
3. extractionThe aqueous phase was extracted with ether
4. washwashed with water
5. dry with materiala saturated sodium chloride solution in that order and then dried
6. customAfter removing the drying agent
7. filtrationby filtering
8. distillationthe solvent was distilled off under reduced pressure
9. customThe residue was purified by silica gel chromatography

ORD record

ord-ec951659cf22488498e9b4b44fa9130d

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07667078B2