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Olefination of 3-phenyl-1H-indene to Benzofulvene; (1E)-1-(3-chlorobenzylidene)-3-phenyl-1H-indene

SyntheticPage 779
DOI: 10.1039/SP779
Submitted May 06, 2015, published May 08, 2015
Adam Glass (glassac@plu.edu), Katie Caspary (casparke@plu.edu), John Fordice (fordicjw@plu.edu), Christian Rude (rudeci@plu.edu)
A contribution from GlassLab, Pacific Lutheran University


			Reaction Scheme: <IMG src="/images/empty.gif">Olefination of <SPAN id=csm1431339768880 class=csm-chemical-name title=3-phenyl-1H-indene grpid="2">3-phenyl-1<EM>H</EM>-indene</SPAN> to Benzofulvene<IMG src="/images/empty.gif">

Chemicals Used

3-phenyl-1H-indene (Prepared in House by method of SP696)

3-chlorobenzaldehyde (Oakwood Chemical, 95%)

1,8-Diazabicyclo[5.4.0]undec-7-ene "DBU" (TCI, 98%)

2-MeTHF (Sigma-Aldrich, HPLC grade)

Procedure

The synthesis was performed under ambient atmosphere. To a microwave reaction vial charged with indene  (0.204 g, 1.06 mmol) was added 3-chlorobenzaldehyde (0.154 g, 1.10 mmol), DBU  (0.172 g, 1.13 mmol), and 2-MeTHF (2 mL, 0.53 M). The vial was then heated via variable watt microwave irradiation to 60 °C for 10 minutes with a 30 second pre-stirring period. Upon completion a yellow sheen was observed on the sides of the vial. The reaction mixture was quenched using a silica plug. The solvent was removed under reduced pressure. The crude mixture was purified via preparative chromatography, (90:10 hexane:toluene) yielding the title compound as a crimson red solid, (0.190 g, 58%).

The synthesis was also performed on a 100 mg scale (indene) yielding 90 mg of the title compound (55%). 

Author's Comments

3-chlorobenzaldehyde should be added before the DBU, and the time between the addition of the DBU and microwave heating should be minimized in order to maximize yield.

Data

1H NMR (CDCl3, 500 MHz): δ ppm 7.06 (s, 1H), 7.29-7.36 (m, 4H), 7.39-7.44 (m, 2H), 7.46-7.51 (m, 3H), 7.59-7.62 (m, 2H), 7.69-7.75 (m, 3H)

 13C NMR (CDCl3, 125 MHz): δ ppm 119.5, 120.5, 122.5, 125.7, 126.2, 127.60, 127.7, 128.1, 128.2, 128.31,128.6, 129.8, 129.9, 134.6, 135.4, 138.6, 138.8, 140.3, 140.8, 148.3

GC-MS EI [M.+]: Predicted: 314.09, Actual: 314;   Predicted: 315.09 Actual: 315; Predicted: 316.08,  Actual: 3161


Supplementary Information

GC-MS Data (metachlorobenzofulvene GC-MS.pdf)
1H NMR (metachlorobf1HPure.esp)
13C NMR (metachlorobf13CPure.esp)
1H NMR PDF Full (metachlorobf1Hfull.pdf)
1H NMR PDF Zoom (metachlorobf1Hzoom.pdf)
13C NMR PDF Full (metachlorobf13Cfull.pdf)
13C NMR PDF Zoom (metachlorobf13Czoom.pdf)

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Keywords: aldehydes, alkenes, aromatics/arenes