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For an interesting stereoselective Birch reduction of 3-methyl-2-furoates as an entry into 2,5-dihydrofurans, see: T.J. Donohoe, A. Raoof, G.C. Freestone, I.D. Linney, A. Cowley, and M. Helliwell Org. Lett. 4 2002 3059 3062
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Prepared from 1,5-pentanediol via the sequence: (a) NaH, BnBr, THF, Δ (63%); (ii) Swern oxidation (99%)
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20
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18844381968
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note
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3, 4-bromo-2-methyl-2-butene, 2-butanone, rt (94%); (iii) Fe, HCl, EtOH, Δ (82%)
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22
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18844431719
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+]
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23
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C 18.3, 25.6, 25.8, 27.2, 27.7, 28.7, 29.2, 58.7, 63.0, 66.2, 70.2, 76.8 × 2, 87.6, 89.9, 90.3, 99.5, 106.4, 108.2, 112.7, 115.6, 119.1, 125.9, 129.9, 134.9, 137.7, 138.6, 140.6, 144.4, 149.7, 149.7, 154.5, 161.8, 162.2
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