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reactions was not attempted). The reaction gives ready access to a
large number of furan products from the wide range of commer-
cially available ketone and a-haloketone building blocks.
6. Kosugi, M.; Takano, I.; Hoshino, I.; Migita, T. J. Chem. Soc., Chem. Commun. 1983,
989–990.
Acknowledgements
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8. Barba, F.; de la Fuente, J. L. Tetrahedron Lett. 1992, 33, 3911–3914.
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The author thanks the Co-operative Research Centre for Poly-
mers and CSIRO Materials Science and Engineering for their
support.
11. Experimental Procedure. A solution of acetone (2 M in toluene, 4.62 mL of a
25 mL stock solution, 9.24 mmol) pumped at a rate of 0.76 mL minÀ1 was
mixed at ambient temperature with a solution of LiHMDS (1 M in THF, 9.24 mL,
9.24 mmol) pumped at a rate of 1.54 mL minÀ1 via a T-piece and passed
through a 10 mL reactor coil (PFA tubing, 1 mm i.d.). The eluent stream was
then mixed with a solution of phenacyl bromide (1.4 M in THF, 6.00 mL of a
50 mL stock solution, 8.4 mmol) pumped at a rate of 1 mL minÀ1 via a T-piece
(injection time delayed so as to coincide with the enolate stream) and passed
through two 10 mL reactor coils (PFA tubing, 1 mm i.d.). The flow solvent was
toluene. The eluent stream was collected in a flask containing H2O (20 mL),
shaken and the organic phase separated, washed with H2O (20 mL), dried
(MgSO4) and evaporated in vacuo, The residue was then purified by column
chromatography eluting with 0–5% v/v EtOAc/petroleum ether to give 2-
methyl-4-phenylfuran as a white solid (0.33 g, 25%). The product gave a good
spectral comparison with the data previously reported.12
Supplementary data
Supplementary data (experimental procedures and data for all
new compounds) associated with this article can be found, in the
References and notes
1. Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, third ed.; Chapman and
Hall, 1995. pp. 278–300.
2. Shipman, M. Contemp. Org. Synth. 1995, 2, 1–17.
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N. C. Tetrahedron 1998, 54, 1955–2020.
12. Pri-Bar, I.; Pearlman, P. S.; Stille, J. K. J. Org. Chem. 1983, 48, 4629–4634.
4. For recent reviews, see: (a) Yoshida, J.; Kim, H.; Nagaki, A. ChemSusChem 2011,
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Wegner, J.; Ceylan, S.; Kirschning, A. Chem. Commun. 2011, 47, 4583–4592.