Water → 2-(4-Nitrophenyl)propanenitrile
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=O)=[CH:6][CH:5]=1)=O.S([CH2:23][N+:24]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CC(C)([O-])C.[K+].[OH2:32]>COCCOCCOC.C(O)(C)(C)C>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:2]([CH3:1])[C:23]#[N:24])=[CH:9][CH:8]=1)([O-:12])=[O:32]Participants
Conditions
- Temperature
- -15 °C
Procedure
A −15° C. solution of 4-nitroacetophenone (16.5 g, 100 mmol) and tosylmethyl isocyanide (29.3 g, 150 mmol) in methoxyethyl ether (400 mL) was slowly treated with a room temperature solution of the potassium t-butoxide (28 g, 250 mmol) in t-butanol (200 mL). The reaction mixture was stirred at −15° C. for 1 h and then allowed to warm to room temperature over night. Water (100 mL) was added to the mixture and organic was extracted with ether (3×200 mL). The combined organic fraction was washed with water (3×200 mL), brine (100 mL), dried over sodium sulfate, and concentrated in vacuo to give the crude material which was further purified by flash chromatography (SiO2, 30% EtOAc:Hexanes) to give 13.6 g (77%) of the title compound. The NMR spectrum was consistent with the proposed title structure. Field Desorption Mass Spectrum: M+=225.
Workup
- temperatureto warm to room temperature over night
- extractionorganic was extracted with ether (3×200 mL)
- washThe combined organic fraction was washed with water (3×200 mL), brine (100 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customto give the crude material which
- customwas further purified by flash chromatography (SiO2, 30% EtOAc:Hexanes)
Sources & evidence
- ORD record
- ord-b61071a4b62f4438a951e20ce8d87c84
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06617351B1
Reaction notes
Loading…