Acetic Acid → Ethyl 2-cyano-2-cyclopentylideneacetate
Reaction equation
C[Si](C)(C)N[Si](C)(C)C.C(O)(=O)C.[C:14]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21]>O.C(OCC)(=O)C>[C:20]([C:22](=[C:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To an ambient solution of hexamethyldisilazane (17.7 mL, 84.0 mmol) m acetic acid (56 mL) was added sequentially cyclopentanone (5.0 mL, 56.3 mmol) and ethyl 2-cyanoacetate (12.0 mL, 113 mmol). The solution was heated to 70° C. for 15 hours. The reaction was cooled to room temperature and diluted with water (100 mL) and ethyl acetate (100 mL). The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×100 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 gel, eluting with 100% hexane to 5% ethyl acetate in hexane, to give the title product as a white, solid. MS (ESI) m/z 180 [M+H]+.
Workup
- temperatureThe reaction was cooled to room temperature
- customThe layers were separated
- extractionthe aqueous was extracted with additional ethyl acetate (2×100 mL)
- dry with materialThe combined organics were dried with anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by chromatography on SiO2 gel
- washeluting with 100% hexane to 5% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-71894b9091014390ad495f3f28f93d5f
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242139B2
Reaction notes
Loading…