Triethylamine → 4-Methyl-4-nitropentyl methanesulfonate

4-Methyl-4-nitropentanol (4.3 g, 29.2 mmol) was dissolved in methylene chloride (100 ml) and triethylamine (6.1 ml, 43.8 mmol) was added, which was followed by ice-cooling. Methanesulfonyl chloride (2.94 ml, 38.0 mmol) was added and the mixture was stirred for 1 h under ice-cooling. The mixture was washed with water (50 ml), 0.5 mol/L hydrochloric acid (50 ml), 5% aqueous sodium hydrogencarbonate solution (50 ml) and saturated brine (50 ml). Methylene chloride was evaporated by concentration under reduced pressure and the residue was subjected to crystallization with ethyl acetate (4 ml) and n-hexane (20 ml). After filtration, the residue was dried under reduced pressure at 40° C. to give the objective compound (6.17 g, yield 93.8%).

1. temperaturecooling
2. temperaturecooling
3. washThe mixture was washed with water (50 ml), 0.5 mol/L hydrochloric acid (50 ml), 5% aqueous sodium hydrogencarbonate solution (50 ml) and saturated brine (50 ml)
4. customMethylene chloride was evaporated by concentration under reduced pressure
5. customthe residue was subjected to crystallization with ethyl acetate (4 ml) and n-hexane (20 ml)
6. filtrationAfter filtration
7. customthe residue was dried under reduced pressure at 40° C.

ORD record

ord-7824b3405d304f88800ea966dbc8e7f8

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06664412B2