Next Article in Journal
Synthesis of 3-Bromo-2-ethoxy-4-methyl-3,4-dihydro-2H-pyran-6-amide
Previous Article in Journal
[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Diacetate
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

Synthesis of 3-Bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-amide

Institute of Organic Chemistry, University of Lausanne, BCH, CH-1015 Lausanne-Dorigny, Switzerland
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(7), M23; https://doi.org/10.3390/M23
Submission received: 20 June 1997 / Published: 4 July 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Scheme.
Scheme.
Molecules 02 m23 sch001
The amide 2 [1] was prepared by hydrolysis of the nitrile 1 according to the reported procedure [2].
To a cooled (0deg.C) solution of 1 (232 mg, 1 mmol) in CH2Cl2 (1 ml) was added successively hydrogen peroxide (30%, 0.5 ml), tetra-(n-butyl)ammonium hydrogen sulfate (70 mg) and an aqueous solution of sodium hydroxide (20%, 0.38 ml). The reaction mixture was allowed to warm to room temperature. Methylenechloride (15 ml) was added after 1 h. The organic layer was separated, washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue (0.25 g) was flash chromatographed (AcOEt/Hexane = 3:1) to afford 200 mg (80%) of 2.
Rf (AcOEt): 0.50.
M. p. 141-142 deg.C.
IR (cm-1, KBr): 3400vs, 3260vs, 1674vs, 1635vs, 1610vs, 1410vs, 975vs, 847s, 810s, 765s.
1H-NMR (CDCl3): 6.33 (br, 1H, NH); 6.26 (br, 1H, NH); 6.06 (dd, J = 5.2, 3.0, 1H, H-5); 5.16 (d, J = 2.1, 1H, H-2), 4.12 (ddd, J = 10.4, 6.3, 2.1, 1H, H-3); 3.87 and 3.71 (2x dq, J = 9.7, 7.1, OCH2Me), 2.77 (ddd, J = 18.2, 10.4, 3.0, 1H, H-4); 2.63 (ddd, J = 18.2, 6.3, 5.2, 1H, H-4); 1.26 (t, J = 7.1, 3H, Me).
13C-NMR (CDCl3): 163.9 (CONH2), 141.5 (C-6), 107.5 (C-5), 97.6 (C-2), 65.2 (OCH2Me), 43.1 (C-3), 27.8 (C-4), 14.8 (OCH2CH3).
CI-MS: 269/267 (M+NH4+, 82/74), 253/251 (M+2, 9/9), 252/250 (M+H+, 87/87), 170 (M-Br, 100), 152/150 (7/7), 125 (31), 124 (41), 99 (9), 97 (21), 85 (11), 77 (31).

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgment

We thank the Swiss National Foundation for financial support.

References

  1. Zhuo, J.-C.; Wyler, H. Helv. Chim. Acta 1995, 78, 151.
  2. Cacchi, S.; Misiti, D.; La Torre, F. Synthesis 1980, 243.
  • Sample Availability: Available from MDPI, 0.1g, MDPI 12539.

Share and Cite

MDPI and ACS Style

Zhuo, J.-C.; Wyler, H. Synthesis of 3-Bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-amide. Molecules 1997, 2, M23. https://doi.org/10.3390/M23

AMA Style

Zhuo J-C, Wyler H. Synthesis of 3-Bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-amide. Molecules. 1997; 2(7):M23. https://doi.org/10.3390/M23

Chicago/Turabian Style

Zhuo, Jin-Cong, and Hugo Wyler. 1997. "Synthesis of 3-Bromo-2-ethoxy-3,4-dihydro-2H-pyran-6-amide" Molecules 2, no. 7: M23. https://doi.org/10.3390/M23

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop