Lithium Hydroxide → 1,1,1-Trifluoro-3-methyl-2-(nitromethyl)butan-2-ol

A cooled (0° C.) solution of lithium hydroxide (0.048 g, 2.015 mmol) in water (20 ml) was stirred and treated with nitromethane (1.23 g, 20.15 mmol), 1,1,1-trifluoro-3-methylbutan-2-one (3.11 g, 22.17 mmol), cetyltrimethylammonium Chloride (0.871 g, 2.72 mmol) and MgSO4 (0.485 g, 4.03 mmol). The white suspension was stirred at 0° C. for 1 hr, then at RT for 2 days. The resulting biphasic mixture was separated and the more dense lower layer was collected and dissolved in diethyl ether (30 ml). The mixture was dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow oil. The oil was taken up in diethyl ether (10 ml) and passed through a pre-packed SCX-2 cartridge eluting with 100% diethyl ether. The filtrate was concentrated in vacuo to afford the title compound as a colourless oil. 1H NMR (400 MHz, CDCl3):

1. stirringThe white suspension was stirred at 0° C. for 1 hr
2. customThe resulting biphasic mixture was separated
3. customthe more dense lower layer was collected
4. dissolutiondissolved in diethyl ether (30 ml)
5. dry with materialThe mixture was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a pale yellow oil
9. washeluting with 100% diethyl ether
10. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-52a5da53cf38424dbd4d2bd759385b66

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247436B2