Dichloromethane → 4-Methyl-4-nitropentyl methanesulfonate

Temperature

0 °C

Anhydrous DCM (200 mL) was added via canula to a flask containing 4-methyl-4-nitropentanol (12.0 g, 81.8 mmol) under a nitrogen atmosphere. The solution was cooled in an ice bath for 15 minutes and triethylamine (17.1 mL, 1.5 equiv, 123 mmol) was added followed by the addition of methanesulfonyl chloride (8.23 mL, 1.3 equiv, 106 mmol) via syringe over one min. The mixture was stirred for 1 h at 0° C. Then water (100 mL) was added and the layers were separated. The organic layer was washed with 1 M HCl (100 mL), saturated NaHCO3 solution (100 mL) and brine (100 ml). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give a liquid which crystallized upon addition of a mixture of 20% EA in hexanes (50 mL). The solid was filtered and dried under high vacuum to give a white solid (14.3 g, 78%). 1H NMR (CDCl3, 400 MHz): δ 1.61 (s, 6H), 1.73-1.77 (m, 2H), 2.02-206 (m, 2H), 3.02 (s, 3H), 4.23 (t, 2H). LRMS (ESI+) for C7H15NO5S (225.1); Found: 226 (MH+).

1. temperatureThe solution was cooled in an ice bath for 15 minutes
2. customthe layers were separated
3. washThe organic layer was washed with 1 M HCl (100 mL), saturated NaHCO3 solution (100 mL) and brine (100 ml)
4. dry with materialThe organic layer was dried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customto give a liquid which
8. customcrystallized upon addition of a mixture of 20% EA in hexanes (50 mL)
9. filtrationThe solid was filtered
10. customdried under high vacuum

ORD record

ord-0d9cd63def594218a2aa07f6028af265

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2