(S)-tert-butyl 5,6-di(nitrooxy)hexanoate → (S)-5,6-di(nitrooxy)hexanoic acid
Reaction equation
[N+:1]([O:4][C@H:5]([CH2:16][O:17][N+:18]([O-:20])=[O:19])[CH2:6][CH2:7][CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])([O-:3])=[O:2]>C(Cl)Cl>[N+:1]([O:4][C@H:5]([CH2:16][O:17][N+:18]([O-:20])=[O:19])[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])([O-:3])=[O:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-tert-butyl 5,6-di(nitrooxy)hexanoate (12.41 g, 42.155 mmol) in DCM (47 mL) cooled to 0° C. under N2, boron trifluoride diethyl ether complex (5.82 mL, 46.37 mmol) was added. The reaction mixture was stirred at 0° C. for 10 minutes and at rt for 3 hrs. The solution was washed with brine, the organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The crude brown oil was used in the next step without further purification.
Workup
- additionboron trifluoride diethyl ether complex (5.82 mL, 46.37 mmol) was added
- washThe solution was washed with brine
- customthe organic layer was separated
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude brown oil was used in the next step without further purification
Sources & evidence
- ORD record
- ord-7f70f1c27bc1477b949291bd75e25437
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119806B2
Reaction notes
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