Ethanol, 1-ethoxy-2,2,2-trifluoro- → (2SR)-(3SR)-3-nitro-1,1,1-trifluoro-2-heptanol
Reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([O-:3])=[O:2].C([O:11][CH:12](O)[C:13]([F:16])([F:15])[F:14])C.C(=O)([O-])[O-].[K+].[K+]>CC(=O)OCC>[N+:1]([CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[CH:12]([OH:11])[C:13]([F:16])([F:15])[F:14])([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of 1-nitropentane (1.0 g, 8.5 mmol) and trifluoroacetaldehyde ethyl hemiacetal (1.2 mL, 8.5 mL) was added potassium carbonate (K2CO3 ) (0.06 g, 0.43 mmol). The reaction mixture was heated at 60° C. under Ar for 3 h. The mixture was cooled to R.T., then taken up in EA (50 mL). The organic layer was washed with 1N HCl (2×10 mL), sat. NaCl (2×10 mL), dried (MgSO4), filtered and concentrated to give (2SR)-(3SR)-3-nitro-1,1,1-trifluoro-2-heptanol as a crude oil (1.7 g, 93%): 1H NMR (CDCl3, 300 MHz) δ 0.91 (t, 3 H, J=7.2 Hz), 1.24-1.43 (m, 4 H), 2.04-2.11 (m, 2 H), 4.08-4.77 (m, 3 H) ppm.
Workup
- temperatureThe mixture was cooled to R.T.
- washThe organic layer was washed with 1N HCl (2×10 mL), sat. NaCl (2×10 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6acde01096614c9a9f174d138327dee5
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05804560
Reaction notes
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