Dimethylformamide → 8-Chloro-2,2-dimethylchroman-6-carbaldehyde

Temperature

-78 °C

6-Bromo-8-chloro-2,2-dimethyl-3,4-dihydro-2H-chromene (483 mg, 1.75 mmol) in THF (8.76 mL) was cooled to −78° C. and n-BuLi (841 μL, 2.10 mmol) was added dropwise via a syringe. The reaction mixture was stirred at −78° C. for 10 minutes and then DMF (543 μL, 7.01 mmol) was added dropwise via a syringe. The resulting mixture was allowed to warm to room temperature, and wet silica gel (5.0 g/0.5 mL of water) was added. The mixture was allowed to stir at room temperature for 10 minutes before it was filtered. The silica gel was rinsed with EtOAc, and the filtrate was concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to obtain the desired product as a pale-yellow oil.

1. temperatureto warm to room temperature
2. additionwet silica gel (5.0 g/0.5 mL of water) was added
3. stirringto stir at room temperature for 10 minutes before it
4. filtrationwas filtered
5. washThe silica gel was rinsed with EtOAc
6. concentrationthe filtrate was concentrated under vacuum
7. customThe crude mixture was purified by silica gel chromatography
8. washeluting with 0-15% EtOAc/hexanes

ORD record

ord-aa66b56e2a284a1faad48857c9ada305

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2