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DOI: 10.1055/s-0031-1289555
A New Synthesis of trans-2,3-Diaryloxiranes and 2-(1H-Benzo[d][1,2,3]-
triazol-1-yl)-1-arylethanols
via the Reactions of 1-Benzyl-3-methylbenzo-
triazolium
Ylide with Aryl Aldehydes
Publication History
Publication Date:
25 October 2011 (online)
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Abstract
1-Benzyl-3-methylbenzotriazolium ylide was formed by the reaction of 1-benzyl-3-methylbenzotriazolium iodide with t-BuOK. Subsequently it reacted with various aryl aldehydes to give the corresponding trans-2,3-diaryloxiranes and 2-(1H-benzo-[d][1,2,3]triazol-1-yl)-1-arylethanols in moderate to high yields.
Key words
ammonium ylide - 2,3-diaryloxirane - benzotriazole - Darzens reaction - 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-arylethanol
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Li A.-H.Dai L.-X.Aggarwal VK. Chem. Rev. 1997, 97: 234 -
1b
Aggarwal VK.Ford JG.Fonquerna S.Adams H.Jones RVH.Fieldhouse R. J. Am. Chem. Soc. 1998, 120: 8328 -
1c
Aggarwal VK.Winn CL. Acc. Chem. Res. 2004, 37: 611 -
1d
McGarrigle EM.Myers EL.Illa O.Shaw MA.Riches SL.Aggarwal VK. Chem. Rev. 2007, 107: 5841 -
1e
Illa O.Arshad M.Ros A.McGarrigle EM.Aggarwal VK. J. Am. Chem. Soc. 2010, 132: 1828 -
2a
Jonczyk A.Konarska A. Synlett 1999, 1085 -
2b
Kowalkowska A.Sucholbiak D.Jonczyk A. Eur. J. Org. Chem. 2005, 5: 925 -
2c
Kimachi T.Kinoshita H.Kusaka K.Takeuchi Y.Aoe M.Ju-ichi M. Synlett 2005, 842 -
2d
Robiette R.Conza M.Aggarwal VK. Org. Biomol. Chem. 2006, 4: 621 -
2e
Alex A.Larmanjat B.Marrot J.Couty F.David O. Chem. Commun. 2007, 2500 -
2f
Kinoshita H.Ihoriya A.Ju-ichi M.Kimachi T. Synlett 2010, 2330 -
2g
Waser M.Herchl R.Mueller N. Chem. Commun. 2011, 47: 2170 - 3
Hunter EPL.Lias SG. J. Phys. Chem. Ref. Data 1998, 27: 413 - 4
Xiao X.-H.Lin D.-Q.Tong S.-T.Luo H.He Y.-F.Mo H.-L. Synlett 2011, 1731 - 7
Katritzky AR.Wu J.Kuzmierkiewicz W.Rachwal S. Liebigs Ann. Chem. 1994, 1
References and Notes
Process A: BMeBt iodide (1; 3 mmol), benzaldehyde (2a; 3 mmol), t-BuOK (3 mmol) and solvent (10 mL) were mixed together and stirred at r.t. After the purple color of the solution had faded, H2O (25 mL) was added and the products were extracted with EtOAc (3 × 25 mL). The combined organic phases were washed with brine (2 × 25 mL) and H2O (25 mL), and then were dried over anhyd Na2SO4, filtered and concentrated in vacuo. The residue was separated by column chromatography.
6Process B: A solution of BMeBt iodide (1; 3 mmol) and aryl aldehyde 2 (6 mmol) in DMSO (5 mL) was added dropwise to the stirred solution of t-BuOK (6 mmol) in t-BuOH (5 mL) at r.t. After the purple color of the solution had faded, H2O (25 mL) was added and the products were extracted with EtOAc (3 × 25 mL). The combined organic phases were washed with brine (2 × 25 mL) and H2O (25 mL), and then were dried over anhyd Na2SO4, filtered and concentrated in vacuo. The residue was separated by column chromatog-raphy to afford the corresponding trans-2,3-diaryloxiranes 3 and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-arylethanol 4.