Methyl chloroformate → HCID 66701283, compound

Temperature

-20 °C

To a stirred solution of 0.30 g of 4-fluoro-1-methoxymethoxy-naphthalene in 21 ml of dry THF was added 1.8 ml of TMEDA. The mixture was cooled to −18 to −22° C. (carbon tetrachloride bath) after which was added 2.46 ml of 1.6 M n-butyl-lithium. The mixture was stirred at −20° C. for 0.5 h after which it was cooled to −75° C. To the mixture was added a solution of 0.60 ml of methyl chloroformate in 6 ml of THF. The mixture was stirred at −75 to −78° C. for 0.5 h, poured into brine, extracted twice with ether, dried (sodium sulphate), filtered and concentrated to an orange oil. The oil was dissolved in dichloromethane and purified by flash chromatography on silica gel, eluting with ethyl acetate/heptanes to provide 0.162 g of 4-fluoro-1-methoxymethoxynaphthalene-2-carboxylic acid methyl ester as an off-white solid.

1. temperaturewas cooled to −75° C
2. stirringThe mixture was stirred at −75 to −78° C. for 0.5 h
3. extractionextracted twice with ether
4. dry with materialdried (sodium sulphate)
5. filtrationfiltered
6. concentrationconcentrated to an orange oil
7. dissolutionThe oil was dissolved in dichloromethane
8. custompurified by flash chromatography on silica gel
9. washeluting with ethyl acetate/heptanes

ORD record

ord-8a2abfe079c34664ba4653546b2ade23

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08283479B2