Furfural → HCID 67109386, compound

Temperature

-75 °C

To a solution of 5-fluoro-2-iodo-1,3-xylene (11 g, 44 mmol) in tetrahydrofuran (110 ml) is added 1.6 molar solution of n-butyl lithium in hexane (33 ml, 52 mmol) under nitrogen atmosphere at −75° C. The resulting solution is stirred at −75° C. for 60 minutes and to this mixture, a solution of furfural (6.3 g, 65.6 mmol) in THF (20 ml) is added over 20 minutes. The resulting solution is stirred at −75° C. for 2 hours. The cooling bath is removed and the mixture is allowed to reach room temperature, and then stirred for 5 hours. The reaction mixture is quenched with ice cold water (1000 ml) and extracted with ethyl acetate (3×250 ml), dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo to give a residue which is purified by flash chromatography (hexane/ethyl acetate) to afford (4-Fluoro-2,6-dimethylphenyl)furan-2-ylmethanol (6 g).

1. stirringThe resulting solution is stirred at −75° C. for 2 hours
2. customThe cooling bath is removed
3. customto reach room temperature
4. stirringstirred for 5 hours
5. customThe reaction mixture is quenched with ice cold water (1000 ml)
6. extractionextracted with ethyl acetate (3×250 ml)
7. dry with materialdried over anhydrous sodium sulphate
8. filtrationfiltered
9. concentrationthe filtrate is concentrated in vacuo
10. customto give a residue which
11. customis purified by flash chromatography (hexane/ethyl acetate)

ORD record

ord-5def3c44b574403bb7c2c9befb3c2415

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096560B2