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1-(Pyridin-3-yl)but-2-yn-1,4-diol
 
 
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Short Note

1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol

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), M207; https://doi.org/10.3390/M207
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 m207 i001
The general part of the experimental section [1] has been presented elsewhere. nBuLi (1.6 M) (1.9 ml, 5.9 mmol) was added dropwise to a solution of silyl ether 1 (500 mg, 2.94 mmol) in THF (10 mL) at 78 oC under nitrogen and stirred for 45 min. Pyridine-3-carboxaldehyde 2 (315 mg, 2.94 mmol) was added dropwise and the resultant solution stirred for 1.5 h. The mixture was warmed to room temperature then water (10 mL) was added. The mixture was extracted with ethyl acetate (4 15 mL) and dried over magnesium sulfate. The solvent was removed under reduced pressure to give a yellow oil which was purified by flash chromatography using hexane-ethyl acetate (1:2) as eluent to afford the title compound 3 (773 mg, 95%) as a pale yellow oil.
IR (neat): 3308b, 2957s, 2913s, 2877s, 2235w, 1741s, 1591m, 1243s.
1H NMR (200 MHz, CDCl3): 0.63 [6H, q, J 8.0 Hz, OSi(CH2CH3)3], 0.96 [9H, t, J 8.0 Hz, OSi(CH2CH3)3], 4.40 (2H, d, J 1.8 Hz, H4), 5.56 (1H, br. s, H1), 7.31 (1H, m, H5'), 7.88 (1H, ddd, J5',4' 7.4, J4',6' 1.7 and J2',4' 1.7 Hz, H4'), 8.56 (1H, dd, J6',4' 1.7 and J6',5' 4.8 Hz, H6'), 8.75 (1H, d, J2',4' 1.7 Hz, H2').
13C NMR (50 MHz, CDCl3): 4.3 [CH2, OSi(CH2CH3)3], 6.6 [CH3, OSi(CH2CH3)3], 51.3 (CH2, C4), 62.0 (CH, C1), 83.8 (quat., C3), 85.4 (quat., C2), 123.5 (CH, C5'), 131.8 (CH, C4'), 136.9 (CH, C6'), 147.7 (CH, C2'), 148.7 (quat., C3').
EI-MS: 277 (M+, 10%), 248 (M+-C2H5, 47%), 162 (M+-Si(CH2CH3)3, 66%), 146 (70%), 117 (59%), 103 (84%), 75 (100%).
Anal. Calc. For C15H23NO2Si, 277.14981; found M+, 277.14918.

References

  1. Brimble, M. A.; Duncalf, L. J. Molecules 2000, 5, 162–166. [CrossRef]
Sample Availability: available from the authors and MDPI.

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MDPI and ACS Style

Caprio, V.E.; Jones, M.W.; Brimble, M.A. 1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol. Molecules 2001, 6, M207. https://doi.org/10.3390/M207

AMA Style

Caprio VE, Jones MW, Brimble MA. 1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol. Molecules. 2001; 6(3):M207. https://doi.org/10.3390/M207

Chicago/Turabian Style

Caprio, Vittorio E., Michael W. Jones, and Margaret A. Brimble. 2001. "1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol" Molecules 6, no. 3: M207. https://doi.org/10.3390/M207

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