Hydrochloric Acid → 3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclopenten-1-one

Temperature

-78 °C

1,3-Bis(methoxymethoxy)-4-bromobenzene (1.0 g) was dissolved in THF (20 ml) and cooled to −78° C. under argon. N,N,N′,N′-Tetramethylethylene diamine was added followed by dropwise addition of n-BuLi (3.4 ml of a 2.2M solution in hexanes) over 10 mins. After stirring at −78° C. for 1 hr, a solution of 3-methoxy-2-cyclopentene-1-one (605 mg) in THF (5 ml) was added slowly. The reaction mixture was stirred at −78° C. for 1 hr before warming to 0° C. 1 M HCl (20 ml) was added, and after 10 min the mixture was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with brine (30 ml), dried over magnesium sulfate, and concentrated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish the title compound as yellow oil (128 mg, 13%); m/z (ES+) 279 (M+1)+.

1. stirringThe reaction mixture was stirred at −78° C. for 1 hr
2. temperaturebefore warming to 0° C
3. extractionafter 10 min the mixture was extracted with ethyl acetate (2×50 ml)
4. washThe combined organic phases were washed with brine (30 ml)
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v)

ORD record

ord-3d18af38d4fb41239af33deadd6aabae

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06828460B2