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Short Note

5-Methoxy-7,7-dimethyl-1,9(E),11-dodecatrien-3-ol

The DASGroup, Inc., 1732 Lyter Drive, 2nd Floor, Johnstown, Pennsylvania 15905-1206, USA, and Department of Chemistry, University of Toledo, Toledo, Ohio 43606-3390, USA
Molecules 1997, 2(10), M37; https://doi.org/10.3390/M37
Submission received: 29 September 1997 / Published: 31 October 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Scheme 
Scheme 
Molecules 02 m37 sch001
To a stirred solution of the diene aldehyde [1] in dry THF under Ar at -78 fC, vinylmagnesium bromide in THF was added via a syringe. The reaction was stirred for 15 minutes then quenched at -78 fC with sat aq sodium potassium tartrate and stirred while warming to room temperature. The mixture was extracted with pet ether and the combined organic layers dried over Na2SO4 and concentrated to give a 1 : 1 diastereomeric mixture of the triene alcohols as a colorless oil in 69 percent yield.
1H NMR (CDCl3): d: 6.30 (dt, J = 17.0, 10.2Hz, 1H), 6.01 (bdd, J = 14.8, 10.6Hz, 1H), 5.84 (ddd, J = 17.1, 10.7, 5.8Hz, 1H), 5.70 (dt, J = 15.1, 7.5Hz, 1H), 5.26 (dd, J = 14.1, 7.6Hz, 1H), 5.1 - 5.04 (m, 2H), 4.94 (d, J = 10.0Hz, 1H), 4.38 (m, CHOH), 4.21 (m, CHOH), 3.54 (m, CHOMe), 3.44 (M, CHOMe), 3.30 (s, OMe), 3.28 (s, (OMe), 3.25 (bs, OH), 2.90 (bs, OH), 1.99 (d, J = 7.5Hz, 2H), 1.9 - 1.48 (m, 3H), 1.35 - 1.25 (m, 1H), 0.91 (s, 3H), 0.87 (s, 3H).
IR (CDCl3): 3600, 3450, 2960, 2940, 2830, 1645, 1600, 1460, 1425, 1390, 1370, 1085, 1010, 890.
MS (m/e): 238 (M+, 2), 223, 205, 198, 169, 115, 113, 108 (100), 99, 94, 93, 59.
HRMS: calc. for C14H21O: (M - CH5O): 205.1592; found: 205.1593.

Supplementary materials

Supplementary File 1Supplementary File 2

References and Notes

  1. Smith, D. 3-Methoxy-5,5-dimethyl-7(E),9-decadienal. Molecules 1997, 2, M36. [Google Scholar]
  • Sample Availability: No sample available.

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MDPI and ACS Style

Smith, D.A. 5-Methoxy-7,7-dimethyl-1,9(E),11-dodecatrien-3-ol. Molecules 1997, 2, M37. https://doi.org/10.3390/M37

AMA Style

Smith DA. 5-Methoxy-7,7-dimethyl-1,9(E),11-dodecatrien-3-ol. Molecules. 1997; 2(10):M37. https://doi.org/10.3390/M37

Chicago/Turabian Style

Smith, Douglas A. 1997. "5-Methoxy-7,7-dimethyl-1,9(E),11-dodecatrien-3-ol" Molecules 2, no. 10: M37. https://doi.org/10.3390/M37

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