Methyl N-(triethylammoniosulfonyl)carbamate → (3,3,3-Trifluoro-1-nitroprop-1-enyl)cyclohexane
Reaction equation
[CH:1]1([CH:7]([N+:14]([O-:16])=[O:15])[CH:8](O)[C:9]([F:12])([F:11])[F:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1C=CC=CC=1>[F:10][C:9]([F:11])([F:12])[CH:8]=[C:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[N+:14]([O-:16])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 3-cyclohexyl-1,1,1-trifluoro-3-nitropropan-2-ol (2) (1.015 gm) and ([methoxycarbonylsulfamoyl]triethylammonium hydroxide, inner salt) (Burgess reagent) (2.2 gm) in benzene (10 mL) was heated to 70° C. for 1.5 hours. After cooling the reaction mixture to room temperature, the organic layer was decanted away from the solids and evaporated to dryness under reduced pressure. Purification of the crude product on silica gel chromatography (eluting with 2% ethyl acetate/hexane) gave (3,3,3-trifluoro-1-nitroprop-1-enyl)cyclohexane (0.62 gm, 66%).
Workup
- temperatureAfter cooling the reaction mixture to room temperature
- customthe organic layer was decanted away from the solids
- customevaporated to dryness under reduced pressure
- customPurification of the crude product
- washon silica gel chromatography (eluting with 2% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-2ea8721b9cc1490aaf6cd66e1b60f8b5
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106059B2
Reaction notes
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