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Short Note

tert-Butyl-3-methoxy-5,5-dimethyl-7-hydroxy-8-trimethylsilyl-9-decenoate

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), M33; https://doi.org/10.3390/M33
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 m33 sch001
The crude aldehyde, tert-butyl-3-methoxy-5,5-dimethyl-7-oxo-heptanoate [1] was treated with pinacol E-1-trimethylsilyl-1-propene-3-boronate [2] in petroleum ether at room temperature to provide a 50% yield of the diastereomeric boronic esters, which were simultaneously cleaved to the alcohols and readily separated by flash chromatography.
Following the procedure of Tsai and Matteson [2] the crude aldehyde and pinacol E-1- trimethylsilyl-1-propene-3-boronate were stirred at room temperature in ether for 40 hours and then concentrated. The title compound was obtained as a colorless oil as an 1 : 1 mixture of separable (flash chromatography, 10 : 1 pet ether : ether) diastereoisomers in 50% yield.
Less polar diastereoisomer.
1H NMR (CDCl3): d: 5.83 (dt, J = 17.1, 10.5Hz, 1H), 4.93 (dd, J = 10.5, 2.3Hz, 1H), 4.83 (dd, J = 17.1, 2.3Hz, 1H), 4.0 (m, 1H), 3.68 (m, 1H), 3.33 (s, 3H), 2.54 (dd, J = 14.8, 4.4Hz, 1H), 2.17 (dd, J = 14.8, 8.4Hz, 1H), 1.96 (dd, J = 15.2, 10.2Hz, 1H), 1.7 (dd, J = 14.9, 10.2Hz, 1H), 1.42 (s, 10H), 1.2 - 1.0 (m, 3H), 0.94 (s, 3H), 0.91 (s, 3H), 0.01 (s, 9H).
IR (CDCl3): 3450, 2965, 1720, 1460, 1370, 1255, 1060, 880.
MS (m/e): 316, 315, 284, 283, 226, 203, 194, 171, 157, 143, 127 (100).
HRMS: calc. for C16H32O4Si (M - C4H8): 316.2070; found: 316.2070.
More polar diastereoisomer.
1H NMR (CDCl3): d: 5.81 (dt, 17.1, 10.5Hz, 1H), 5.00 (dd, J = 10.5, 2.2Hz, 1H), 4.88 (dd, J = 17.1, 2.2Hz, 1H), 3.98 (m, 1H), 3.64 (m, 1H), 3.26 (s, 3H), 2.53 (dd, J = 15.0, 4.9Hz, 1H), 2.19 (dd, J = 15.0, 7.9Hz, 1H), 1.89 (d, J = 5.2Hz, 1H), 1.7 - 1.2 (m, 4H), 1.42 (s, 9H), 1.15 - 1.05 (m, 1H), 0.96 (s, 3H), 0.94 (s, 3H), 0.02 (s, 9H).
IR (CDCl3): 3400, 2950, 1715, 1460, 1365, 880.
MS (m/e): 316, 315, 284, 283, 226, 203, 194, 171, 157, 143, 127 (100).
Anal. calc. for C16H32O4Si (M - C4H8): 316.2070; found: 316.2070.

Supplementary materials

Supplementary File 1Supplementary File 2

References and Notes

  1. Smith, D. tert-Butyl-3-methoxy-5,5-dimethyl-7-oxo-heptanoate. Molecules 1997, 2, M32. [Google Scholar] [CrossRef]
  2. Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751.
  • Sample Availability: No sample available.

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MDPI and ACS Style

Smith, D.A. tert-Butyl-3-methoxy-5,5-dimethyl-7-hydroxy-8-trimethylsilyl-9-decenoate. Molecules 1997, 2, M33. https://doi.org/10.3390/M33

AMA Style

Smith DA. tert-Butyl-3-methoxy-5,5-dimethyl-7-hydroxy-8-trimethylsilyl-9-decenoate. Molecules. 1997; 2(10):M33. https://doi.org/10.3390/M33

Chicago/Turabian Style

Smith, Douglas A. 1997. "tert-Butyl-3-methoxy-5,5-dimethyl-7-hydroxy-8-trimethylsilyl-9-decenoate" Molecules 2, no. 10: M33. https://doi.org/10.3390/M33

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