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Short Note

1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime

by
Vittorio E. Caprio
,
Michael W. Jones
and
Margaret A. Brimble
*
Department of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(3), M201; https://doi.org/10.3390/M201
Submission received: 8 December 2000 / Accepted: 15 December 2000 / Published: 25 March 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes

Molecules 06 m201 i001
The general part of the experimental section [1] has been presented elsewhere. Boron trifluoride diethyl etherate (313 mg, 2.21 mmol) was added dropwise to a solution of oxime 1 (100 mg, 0.735 mmol) in toluene (8 mL) at -78oC under nitrogen and the mixture stirred for 5 min. Vinylmagnesium bromide (1 M in THF) (2.2 mL, 2.20 mmol) was added dropwise over 10 min and the resultant orange coloured solution stirred at -78°C for 1.5 h [2]. Water (1 mL) was added and the reaction warmed to room temperature. The mixture was extracted with ethyl acetate (3 x 15 mL), dried over magnesium sulfate and concentrated under reduced pressure to give a dark red solid. Further purification by flash chromatography using diethyl ether-hexane (1:9) gave the title compounds 2 (9 mg, 8%) and (3) (14 mg, 10%) as pale yellow oils.

1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime 2

IR (neat): 2917s, 2847m, 1696m, 1627bm, 1460m, 1054m.
1H NMR (200 MHz, CDCl3): 1.23 (3H, t, J 7.8 Hz, H3), 2.67 (2H, q, J 7.8 Hz, H2), 4.08 (3H, s, OCH3), 5.54 (1H, dd, J 1.9 Hz, J 10.8 Hz, H2″A), 6.26 (1H, dd, J 1.9 Hz, J 17.4 Hz, H2″B), 6.82 (1H, dd, J 10.8 Hz, J 17.4 Hz, H1″), 7.35 (1H, m, H5'), 8.06 (1H, bs, H4'), 8.66 (1H, d, J 2.0 Hz, H6').
EI-MS: 190 (M+, 23%), 189 ((M-H)+, 28%), 159 (100%), 144 (87%), 136 (10%), 91 (12%), 77 (15%).
Anal. Calc. For C11H14N2O, 190.1106; found M+ 190.1103.

1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime 3

IR (cm-1, CH2Cl2): 3053m, 2972m, 2938m, 1452m, 1422m, 1265s, 1054s, 739b, 705s.
1H NMR (200 MHz, CDCl3): 1.24 (3H, t, J 7.6 Hz, H3), 2.67 (2H, q, J 7.6 Hz, H2), 4.01 (3H, s, OCH3), 5.56 (1H, dd, J 1.9 Hz, J 10.8 Hz, H2″A), 6.28 (1H, dd, J 1.9 Hz, J 17.0 Hz, H2″B), 7.06 (1H, dd, J 10.8 Hz, J 17.0 Hz, H1″), 7.87 (1H, d, J4',5' 2.2 Hz, H5'), 8.39 (1H, s, H2'), 8.45 (1H, d, J4',5' 2.2 Hz, H4').
EI-MS: 190 (M+, 26%), 189 ((M-H)+, 28%), 159 (100%), 144 (84%), 130 (11%), 117 (10%), 77 (15%).
Anal. calc. for C11H14N2O (M+), 190.1106; found M+ 190.1099.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4

References

  1. Brimble, M. A.; Duncalf, L. J. Molecules 2000, 5, 162–166. [CrossRef]
  2. Dieter, R.K.; Datar, R. Can. J. Chem. 1993, 71, 814–823.
  • Sample availability: available from the authors.

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MDPI and ACS Style

Caprio, V.E.; Jones, M.W.; Brimble, M.A. 1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime. Molecules 2001, 6, M201. https://doi.org/10.3390/M201

AMA Style

Caprio VE, Jones MW, Brimble MA. 1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime. Molecules. 2001; 6(3):M201. https://doi.org/10.3390/M201

Chicago/Turabian Style

Caprio, Vittorio E., Michael W. Jones, and Margaret A. Brimble. 2001. "1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime" Molecules 6, no. 3: M201. https://doi.org/10.3390/M201

APA Style

Caprio, V. E., Jones, M. W., & Brimble, M. A. (2001). 1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl)propanal O-methyloxime. Molecules, 6(3), M201. https://doi.org/10.3390/M201

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