2-Acetoxy-2-butene → 3-(5-Trifluoromethylbenzofur-7-yl)-2-butanone
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5](Br)[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.CO[Sn](CCCC)(CCCC)CCCC.C([O:33][C:34](=[CH:36][CH3:37])[CH3:35])(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:36]([CH3:37])[C:34](=[O:33])[CH3:35])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 0.27 gm (1.03 mMol) 5-trifluoromethyl-7-bromobenzofuran, 0.50 gm (1.55 mMol) methoxy(tri-n-butyl)tin, 0.18 gm (1.55 mMol) 2-acetoxy-2-butene, and 0.08 gm (0.10 mmol) bis[tri-o-tolylphosphine]palladium(II) chloride in 2.5 mL toluene was heated at 100° C. for 1 hour. The reaction mixture was cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with 10% ethyl acetate in hexane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.090 gm (34%) of the desired compound.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered through a pad of celite
- concentrationThe filtrate was concentrated under reduced pressure
- washeluting with 10% ethyl acetate in hexane
- additionFractions containing product
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-bb72217f563b4126ad8725447ab87c4a
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07045545B1
Reaction notes
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