Furfural → HCID 11171621, compound

In a round-bottomed flask, furan-2-carbaldehyde (800 mg, 8.33 mmol) was dissolved in THF (20 ml) and (S)-2-methylpropane-2-sulfinamide (1.21 g, 10.0 mmol) and titanium(IV) ethoxide (3.5 ml, 16.7 mmol) were added. The reaction mixture was stirred at room temperature for 5 h then slowly quenched by dropwise addition of brine (5 ml) which resulted in the formation of a thick precipitate. The reaction mixture was diluted with ethyl acetate and stirred vigorously at room temperature for 15 min. The suspension was filtered over Celite and rinsed with ethyl acetate. The filtrate was concentrated and the residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-25% EtOAc) to give 1.48 g (89%) of (S)-2-methyl-propane-2-sulfinic acid 1-furan-2-yl-meth-(E)-ylideneamide as a light yellow oil.

1. customthen slowly quenched by dropwise addition of brine (5 ml) which
2. customresulted in the formation of a thick precipitate
3. stirringstirred vigorously at room temperature for 15 min
4. filtrationThe suspension was filtered over Celite
5. washrinsed with ethyl acetate
6. concentrationThe filtrate was concentrated
7. customthe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-25% EtOAc)

ORD record

ord-768016c83d9f49d8b9821d52334d81ef

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2