Dimethylformamide → HCID 86610812, compound
Reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1.C(OCC)(=O)C.[CH3:27][N:28](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:27]#[N:28])[CH:10]=2)[O:5][C:4](=[O:20])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
Trifluoro-methanesulfonic acid 4-methyl-2-oxo-2H-chromen-6-yl ester (10.38 mg, 33.7 mmol), Zn (CN)2 (4.7 g) and Pd(PPh3)4 (3.8 g) were dissolved in DMF (200 mL) at room temperature in a sealed tube. After 10 min, the reaction mixture was heated to 150° C. for 4 h. The reaction mixture was then cooled to room temperature and ethyl acetate (800 mL) was added. The reaction mixture was then poured into a separation funnel, washed with water (2×400 ml) and brine (2×600 ml). The organic layer was dried over sodium sulfate and concentrated. The product was purified on silica gel eluted with 30-80% ethyl acetate in hexanes to yield 4-methyl-2-oxo-2H-chromene-6-carbonitrile as a white powder.
Workup
- temperatureThe reaction mixture was then cooled to room temperature
- additionThe reaction mixture was then poured into a separation funnel
- washwashed with water (2×400 ml) and brine (2×600 ml)
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated
- customThe product was purified on silica gel
- washeluted with 30-80% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-bf47e04577fa4302be2ec02cd32cbb3b
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662975B2
Reaction notes
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