Next Article in Journal
(4R,2'R,3'R,5'R)-3-[5-(tert-Butyldimethylsilyloxy)-1-oxo-2,3-bis(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone
Previous Article in Journal
3-[5-(tert-Butyldimethylsilyloxy)-3-p-nitrobenzoyl-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 5
Issue 2
10.3390/M136
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

3-[5-(tert-Butyldimethylsilyloxy)-3-(3,5-dinitrobenzoyl)-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone

by
Margaret A. Brimble
* and
Josephine S. O. Park
School of Chemistry, University of Sydney, Eastern Ave, Camperdown, NSW 2006, Australia
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(2), M136; https://doi.org/10.3390/M136
Submission received: 20 January 2000 / Accepted: 2 February 2000 / Published: 23 February 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 05 m136 i001
A mixture of alcohol 1 (104 mg, 0.20 mmol) [1], triethylamine (41 l, 0.30 mmol) and 3,5-dinitrobenzoyl chloride (55 mg, 0.24 mmol) in dichloromethane (2 ml) was stirred for 2 h. at 30°C. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate (5 ml), extracted into ethyl acetate (2 x 10 ml), washed with water (2 x 5 ml) and dried over sodium sulfate. Removal of the solvent under reduced pressure and purification of the residue by flash chromatography, using light petroleum-ethyl acetate (8:2) as eluent, gave the title compound 2 (110 mg, 78%) as a colourless oil.
[a]D -40.22 (c 1.217, CHCl3).
IR (cm-1, neat): 1783s, 1737s, 1709s, 1389m, 1109m.
1H NMR (400 MHz, CDCl3): 0.03, 0.04 (6H, s, SiMe2), 0.86 (9H, s, But), 1.19 (3H, d, J6′,5′ 6.0 Hz, H6′), 2.09-2.12 (2H, m, H4′), 2.69 (1H, dd, Jgem 13.5 and J 9.4 Hz, CHCHAPh), 3.20 (1H, dd, Jgem 13.5 and J 3.3 Hz, CHCHBPh), 3.96-4.00 (1H, m, H5′), 4.12 (1H, dd, Jgem 9.1 and J5A,4 7.7 Hz, H5A), 4.17 (1H, dd, Jgem 9.1 and J5B,4 2.8 Hz, H5B), 4.62-4.65 (1H, m, H4), 4.66 (1H, d, Jgem 11.4 Hz, OCHAPh), 4.73 (1H, d, Jgem 11.4 Hz, OCHBPh), 5.56 (1H, d, J2′,3′ 4.0 Hz, H2′), 5.70-5.73 (1H, m, H3′), 7.17-7.38 (10H, m, Ph), 9.13 (2H, d, J 2.1 Hz, PhNO2), 9.21 (1H, t, J 2.1 and J 2.1 Hz, PhNO2).
13C NMR (100 MHz, CDCl3): -4.8, -4.4 (CH3, SiMe2), 18.0 (quat., CMe3), 23.4 (CH3, C6′), 25.8 (CH3, CMe3), 37.5 (CH2, CHCH2Ph), 39.7 (CH2, C4′), 55.6 (CH, C4), 65.6 (CH2, C5), 66.6 (CH, C5′), 73.4 (CH, C3′), 73.5 (CH2, OCH2Ph), 77.9 (CH, C2′), 122.4, 127.5, 128.2, 128.4, 128.5, 129.0, 129.4, 129.5 [CH, 3 x Ph (last 5 peaks coincidental)], 133.8 (quat., CHCH2Ph), 134.7 (quat., OC=OC), 136.9 (quat., OCH2Ph), 148.7 (quat., CNO2), 152.9 (quat., C2) 161.5 (quat., OC=O), 169.2 (quat., C1′).
CI-MS: (FAB, NBA matrix) 722 (MH+, 2%), 664 (4), 614 (MH+-HOCH2Ph, 1), 590 (MH+-HOSiMe2But, 4), 269 (5), 195 (C7H3N2O5, 4), 91 (CH2Ph, 100), 73 (48).
Anal. calc. for C36H43N3O11Si MH+ (CI, NH3), 722.2732; found MH+, 722.2745.

Reference

  1. Brimble, M. A.; Park, J. S. O. J. Chem. Soc. Perkin Trans. I 2000, 697–709.
Sample Availability: Available from the authors.

Share and Cite

MDPI and ACS Style

Brimble, M.A.; Park, J.S.O. 3-[5-(tert-Butyldimethylsilyloxy)-3-(3,5-dinitrobenzoyl)-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone. Molecules 2000, 5, M136. https://doi.org/10.3390/M136

AMA Style

Brimble MA, Park JSO. 3-[5-(tert-Butyldimethylsilyloxy)-3-(3,5-dinitrobenzoyl)-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone. Molecules. 2000; 5(2):M136. https://doi.org/10.3390/M136

Chicago/Turabian Style

Brimble, Margaret A., and Josephine S. O. Park. 2000. "3-[5-(tert-Butyldimethylsilyloxy)-3-(3,5-dinitrobenzoyl)-1-oxo- 2-(phenylmethoxy)hexyl]-4-(phenylmethyl)-2-oxazolidinone" Molecules 5, no. 2: M136. https://doi.org/10.3390/M136

Article Metrics

Back to TopTop