Next Article in Journal
3-Methoxy-5,5-dimethyl-7(E),9-decadien-1-o1
Previous Article in Journal
tert-Butyl-3-methoxy-5,5-dimethyl-7-hydroxy-8-trimethylsilyl-9-decenoate
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 2
Issue 10
10.3390/M34
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

tert-Butyl-3-methoxy-5,5-dimethyl-7(E),9-decadienoate

by
Douglas A. Smith
The DASGroup, Inc., 1732 Lyter Drive, 2nd Floor, Johnstown, Pennsylvania 15905-1206, USA, and Department of Chemistry, University of Toledo, Toledo, Ohio, USA
Molecules 1997, 2(10), M34; https://doi.org/10.3390/M34
Submission received: 29 September 1997 / Published: 31 October 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Browse Figure
Versions Notes
Molecules 02 m34 g001 550
Scheme.
Scheme.
Molecules 02 m34 g001
The diastereomeric alcohols [1], either separately or as a mixture, were converted under acidic Peterson olefination conditions to the title E-diene.
Typically, a mixture of alcohols in dry THF was stirred with a catalytic amount of H2SO4 at room temperature for 19 hours, then washed with sat aq NaHCO3. The aq washings were combined and back extracted with ether. The combined organic layers were washed with sat aq NaCl, dried over Na2SO4 and concentrated to give the title E-diene ester as a colorless oil in 73 percent yield.
1H NMR (CDCl3): δ: 6.29 (dt, J = 16.9, 10.3Hz, 1H), 6.01 (dd, J = 15.3, 10.7Hz 1H), 5.71 (dt, J = 15.3, 7.5Hz, 1H), 5.12 (d, J = 16.9 Hz, 1H), 4.93 (d, J = 10.3Hz, 1H), 3.63 (m, 1H), 3.28 (s, 3H), 2.51 (dd, J = 14.6, 5.4Hz, 1H), 2.21 (dd, J = 14.6, 7.3Hz, 1H), 1.99 (bt, J = 6.2Hz, 2H), 1.6 - 1.3 (m, 1H), 1.43 (s, 9H), 1.27 (dd, J = 14.7, 2.7Hz, 1H), 0.90 (s, 3H), 0.88 (s, 3H).
IR (CDCl3): 2965, 2930, 2830, 1715, 1640, 1600, 1450, 1365, 1295, 1260, 1150.
MS (m/e): 226, 195, 157, 127 (100), 117, 108, 103, 73, 57.
HRMS: calc. for C13H22O3 (M - C4H8): 226.1569; found: 226.1569.

Supplementary materials

Supplementary File 1Supplementary File 2

References and Notes

  1. Smith, D. tert-Butyl-3-methoxy-5,5-dimethyl-7-hydroxy-8-trimethylsilyl-9-decenoate. Molecules 1997, 2, M33. [Google Scholar] [CrossRef]
  • Sample Availability: No sample available.

Share and Cite

MDPI and ACS Style

Smith, D.A. tert-Butyl-3-methoxy-5,5-dimethyl-7(E),9-decadienoate. Molecules 1997, 2, M34. https://doi.org/10.3390/M34

AMA Style

Smith DA. tert-Butyl-3-methoxy-5,5-dimethyl-7(E),9-decadienoate. Molecules. 1997; 2(10):M34. https://doi.org/10.3390/M34

Chicago/Turabian Style

Smith, Douglas A. 1997. "tert-Butyl-3-methoxy-5,5-dimethyl-7(E),9-decadienoate" Molecules 2, no. 10: M34. https://doi.org/10.3390/M34

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