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• W2091777462 abstract "first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessShort Note [2R*,5S*,6S*]-2-Methyl-1,7-dioxaspiro[5.5]undec-3-en-5-ol§ by Margaret A. Brimble * and Andrew D. Johnston Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia * Author to whom correspondence should be addressed. Molecules 1997, 2(6), M15; https://doi.org/10.3390/M15 Received: 16 June 1997 / Published: 20 June 1997 (This article belongs to the Section Molbank Section of Molecules, 1997-2001) Download Download PDF Download PDF with Cover Download XML Download Epub Download Supplementary Material Versions Notes Isomerisations of epoxides to allylic alcohols have been effected by strong non-nucleophilic bases such as lithium dialkylamides. The formation of allylic alcohols from the reaction of epoxides with lithium amide bases appears to proceed via a b-elimination pathway when the reaction is performed in relatively non-polar solvents [1].To a solution of dry diethylamine (0.085 ml, 0.82 mmol) in dry hexane (40 ml) under a nitrogen atmosphere at -35 deg.C, was added n-butyllithium (1.3 ml of a 1.7 mol L solution in hexane, 7.93 mmol) dropwise, and the resultant suspension stirred for 0.5 h. To this was added [2R*,4S*,5S*,6S*]-4,5-epoxy-2-methyl-1,7-dioxaspiro[5.5]undecane (1) (126 mg, 0.68 mmol) via a closed solid addition tube, the suspension allowed to warm to room temperature and stirred for an additional 16 h. After quenching with sodium dihydrogen phosphate solution (10 ml, 10% w/v), the reaction mixture was extracted with ethyl acetate (3x 50 ml). The combined extracts were washed with water (20 ml) and dried over sodium sulphate. Removal of the solvent under reduced pressure gave an orange oil, that was purified by flash chromatography using hexane-ethyl acetate (6:4) as eluent to afford [2R*,5S*,6S*]-2-Methyl-1,7-dioxaspiro[5.5]undec-3-en-5-ol (2, 80 mg, 63%) as colourless needles [2].M.p. 82-83 deg.C.IR (Nujol) cm-1 3640-3200 (br, s, OH), 1650 (w, C=C), 1019 (C-O), 890 (m, C-O).1H-NMR (400 MHz, CDCl3) 1.28 (3H, d, JMe,2 7.0 Hz, Me), 1.47-2.04 (7H, m, 9-CH2, 10-CH2, 11-CH2 and OH), 3.51 (1H, dd, J5,4 5.0 and J5,3 1.8 Hz, 5-H), 3.67 (1H, ddd, J8ax,8eq 11.2, J8ax,9ax 11.2 and J8ax,9eq 3.2 Hz, 8ax-H), 3.73-3.77 (1H, m, 8eq-H), 4.24 (1H, ddq, J2,Me 7.0, J2,3 3.4 and J2,4 1.5 Hz, 2-H), 5.84 (1H, dd, J3,4 10.2 and J3,2 3.4 Hz, 3-H), 5.91 (1H, ddd, J4,3 10.2, J4,5 5.0 and J4,2 1.5 Hz, 4-H).13C-NMR (100 MHz, CDCl3) 18.3, 25.0, 30.8 (CH2, C-9, C-10 and C-11), 20.5 (CH3, Me), 62.9 (CH2, C-8), 64.6 (CH, C-2), 66.6 (CH, C-5), 97.1 (quat, C-6), 124.2, 133.8 (C-3 and C-4).CI-MS 185, (M+H, 40%), 167 (M+H-H2O, 100), 101 (50), 84 (20).Anal. calc. for C10H16O3 C, 65.11; H, 8.56%, M+H (CI, NH3) 185.1180 found C, 65.20; H, 8.75%; M+H, 185.1177. Supplementary materialsSupplementary File 1Supplementary File 2Acknowledgment The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.References and NotesCrandall, J. K. Org. React. 1983, 346. Brimble, M. A.; Johnston, A. D. Another product (3, a colourless oil, 20 mg, 16%) will be reported in the following short note. Molecules 1997, 2, M16. [Google Scholar] [CrossRef] Sample Availability: Available from MDPI, MDPI 11861. Table 1:. Product ratios for allylic and homoallylic alcohols (2) and (3). Table 1:. Product ratios for allylic and homoallylic alcohols (2) and (3). EpoxideSolventProduct Ratio Allylic: HomoallylicOverall Yield1THF 1.0 : 1.373%1Ether/Hexane (2:1) 1.4 :1.074%1Hexane 4.0 : 1.079% © 1997 MDPI. All rights reserved Share and Cite MDPI and ACS Style Brimble, M.A.; Johnston, A.D. [2R*,5S*,6S*]-2-Methyl-1,7-dioxaspiro[5.5]undec-3-en-5-ol§. Molecules 1997, 2, M15. https://doi.org/10.3390/M15 AMA Style Brimble MA, Johnston AD. [2R*,5S*,6S*]-2-Methyl-1,7-dioxaspiro[5.5]undec-3-en-5-ol§. Molecules. 1997; 2(6):M15. https://doi.org/10.3390/M15 Chicago/Turabian Style Brimble, Margaret A., and Andrew D. Johnston. 1997. [2R*,5S*,6S*]-2-Methyl-1,7-dioxaspiro[5.5]undec-3-en-5-ol§ Molecules 2, no. 6: M15. https://doi.org/10.3390/M15 Find Other Styles Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here. Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view." @default.
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