2-(Chloromethyl)furan → HCID 22872533, compound

Temperature

-78 °C

A 1.55M solution of butyllithium (6.45 ml, 10 mmol) in hexane was added by syringe to a stirred solution of (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (1.84 g, 10 mmol) in THF (50 ml) at -78° C. and the solution stirred for 1 hour at -78° C. A solution of 2-chloromethylfuran (1.3 g, 11 mmol) in THF (10 ml) was added gradually and the stirring continued overnight. The solvent was removed under reduced pressure, the residue dissolved in ethyl acetate (50 ml) and extracted with phosphate buffer (pH 7). The water phase was extracted twice with ethyl acetate (2×20 ml ). The organic layer was dried (MgSO4), solvent evaporated under reduced pressure and the residue purified by flash chromatography (diethyl ether/hexane 15/1, silica gel).

1. customthe stirring continued overnight
2. customThe solvent was removed under reduced pressure
3. dissolutionthe residue dissolved in ethyl acetate (50 ml)
4. extractionextracted with phosphate buffer (pH 7)
5. extractionThe water phase was extracted twice with ethyl acetate (2×20 ml )
6. dry with materialThe organic layer was dried (MgSO4), solvent
7. customevaporated under reduced pressure
8. customthe residue purified by flash chromatography (diethyl ether/hexane 15/1, silica gel)

ORD record

ord-411496d5ddec4c59b767540a8c55ee01

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05629293