Dimethyl Carbonate → HCID 86719097, compound

Temperature

-78 °C

To a solution of 6-methylpicolinonitrile (2 g, 16.9 mmol) in THF (20 ml) was added slowly LiHMDS (17 ml, 1M in THF) at −78° C. under N2. Then the reaction mixture was stirred for 1 h at −78° C. and then dimethyl carbonate (1.52 g, 16.9 mmol) was added at −78° C. The mixture was stirred for 30 mins at −78° C. and allowed to 0° C. for 30 mins. Saturated ammonium chloride was added to neutralize to adjust to PH=7-8, the mixture was extracted by ethyl acetate (100 ml*3), the organic layer was dried by sodium sulfate, filtered, concentrated under vacuo to give the residue. The residue was purified by a standard method to give the desired product.

1. stirringThe mixture was stirred for 30 mins at −78° C.
2. waitallowed to 0° C. for 30 mins
3. extractionthe mixture was extracted by ethyl acetate (100 ml*3)
4. dry with materialthe organic layer was dried by sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under vacuo
7. customto give the residue
8. customThe residue was purified by a standard method

ORD record

ord-4ee39e9c5c6b4b32ad9ce479a5cc8cf7

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029531B2