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Short Note

3-Methoxy-5,5-dimethyl-7(E),9-decadien-1-o1

by
Douglas A. Smith
1, 2
1
The DASGroup, Inc., 1732 Lyter Drive, 2nd Floor, Johnstown, Pennsylvania 15905-1206, USA
2
Department of Chemistry, University of Toledo, Toledo, Ohio 43606-3390, USA
Molecules 1997, 2(10), M35; https://doi.org/10.3390/M35
Submission received: 29 September 1997 / Published: 31 October 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 02 m35 i001
To a slurry of LAH (65 mg, 1.7 mmol) in ether (4 ml) at 0 ƒC under Ar, the diene ester [1] (487 mg, 1.7 mmol) in ether (5 ml) was added dropwise. After addition was complete, the reaction was quenched with sat aq Na2SO4. The solution was filtered and the solids were washed with ether (5 x 10 ml). The combined organic layers were dried over Na2SO4 and concentrated to give, after flash chromatography (1 : 1 pet ether : ether) the title alcohol as a colorless oil, 354 mg, in 97 percent yield.
1H NMR (CDCl3): d: 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 = 16.9Hz, 1H), 4.93 (d, J = 10.3Hz, 1H), 3.81 (m, 1H), 3.69 (m, 1H), 3.48 (m, 1H), 3.30 (s, 3H), 2.37 (bm, 2H), 1.99 (d, J = 7.6Hz, 2H), 1.88 (m, 1H), 1.60 (m, 2H), 1.28 (dd, J - 14.7, 4.0Hz, 1H), 0.90 (s, 3H), 0.88 (s, 3H).
IR (CH2Cl2): 3610, 3490, 2930, 1645, 1600, 1460, 1420, 1385, 1075, 1005, 895.
MS (m/e): 212 (M+, 8), 197, 180, 167, 143, 136, 124, 108, 89 (100).
HRMS: calc. for C13H24O2: 212.1776; found: 212.1774.

Supplementary materials

Supplementary File 1Supplementary File 2

References and Notes

  1. Smith, D. tert-Butyl 3-methoxy-5,5-dimethyl-7(E),9-decadienoate. Molecules 1997, 2, M34. [Google Scholar] [CrossRef]
  • Sample Availability: No sample available.

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MDPI and ACS Style

Smith, D.A. 3-Methoxy-5,5-dimethyl-7(E),9-decadien-1-o1. Molecules 1997, 2, M35. https://doi.org/10.3390/M35

AMA Style

Smith DA. 3-Methoxy-5,5-dimethyl-7(E),9-decadien-1-o1. Molecules. 1997; 2(10):M35. https://doi.org/10.3390/M35

Chicago/Turabian Style

Smith, Douglas A. 1997. "3-Methoxy-5,5-dimethyl-7(E),9-decadien-1-o1" Molecules 2, no. 10: M35. https://doi.org/10.3390/M35

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