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Boga, C.1
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33
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37249036201
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General Procedure for the HD Reaction and Quenching with Electrophiles to Compounds 2a-h: To a solution of 5-bromo-2-chlorothiazole (1, 199 mg, 1 mmol, 1 equiv) in anhydrous THF under argon atmosphere a freshly prepared solution of LDA (1.2 equiv) in anhydrous THF was added at -80°C and the mixture stirred at that temperature until TLC analysis showed complete HD reaction (15-20 min, Then the corresponding electrophile (1.5 equiv) was added at -80°C and the reaction was allowed to warm to r.t. The reaction mixture was poured into 2 N HCl and the aqueous phase was extracted with Et 2O. The organic layer was washed with 2 N HCl (2x, H2O (2x) and brine 2x, dried over Na2SO4, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified either by column chromatography or by Kugelrohr distillation
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4, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified either by column chromatography or by Kugelrohr distillation.
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34
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37249091387
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3): δ = 72.9 (s, C5), 132.6 (s, C4), 156.3 (s, C2).
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3): δ = 72.9 (s, C5), 132.6 (s, C4), 156.3 (s, C2).
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35
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37249008367
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3): δ = 132.1 (s), 134.9 (s), 160.1 (s, C2), 181.9 (d, CHO).
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3): δ = 132.1 (s), 134.9 (s), 160.1 (s, C2), 181.9 (d, CHO).
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