Hydrochloric Acid → (5-(Benzyloxy)-2-methoxyphenyl)(5-methylthiazol-2-yl)methanone

온도

-78 °C

To a stirring mixture of 5-methylthiazole (3.80 g, 38.2 mmol) in dry THF (200 mL) was added n-BuLi (2.5 M in hexane, 15.3 mL, 38.2 mmol) drop wise over 20 minutes at −78° C. under nitrogen atmosphere. The mixture was stirred between −78° C. and −60° C. for 1.5 h and then cooled to −78° C. A solution of methyl 5-(benzyloxy)-2-methoxybenzoate (10.4 g, 38.2 mmol) in THF (50 mL) was added drop wise over 30 minutes. The resulting mixture was stirred at −78° C. for 30 minutes and warmed to room temperature with stirring overnight. The mixture was cooled to 0° C. and treated with water (50 mL). The resulting mixture was adjusted to pH around 6 with HCl (1N). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (3:1) to afford (5-(benzyloxy)-2-methoxyphenyl)(5-methylthiazol-2-yl)methanone (2.5 g, 19%) as a yellow gel. 3.0 g of starting material methyl 5-(benzyloxy)-2-methoxybenzoate was recovered.

1. stirringThe resulting mixture was stirred at −78° C. for 30 minutes
2. temperaturewarmed to room temperature
3. stirringwith stirring overnight
4. temperatureThe mixture was cooled to 0° C.
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography
9. washeluting with petroleum ether/EtOAc (3:1)

ORD 기록

ord-4d1da62d272d454e8779d666350e3edf

출처 데이터셋

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09150526B2