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59849126218
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note
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Synthesis of 4,6,6-trimethoxy-1,1,1-trifluorohex-3-en-2-one (1). General procedure: To an ice-cold stirred mixture of 1,1,3,3-tetramethoxybutane (30 mmol), pyridine (60 mmol), and anhydrous chloroform (30 mL) was added dropwise pure trifluoroacetic anhydride (60 mmol), and after completion of the slow addition, the mixture was stirred for 24 more hours at room temperature. Then, the mixture was washed with aqueous solution of hydrochloric acid 0.1 M (3 × 15 mL) and water (2 × 15 mL), and was dried with magnesium sulfate. The solvent was evaporated to give the practically pure products 3. The pure compound was obtained by distillation under reduced pressure (65% yield).
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59849128905
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note
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3, J = 292), 101.5 (C-6), 92.2 (C-3), 56.6 (C-6a-b), 53.1 (C-4a), 37.6 (C-5).MS: m/z (%) = 211 (66), 179 (71), 141 (36), 75 (100).Anal. Calcd: C, 44.63; H, 5.41. Found: C, 44.85; H, 5.13.
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30
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59849120892
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note
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Synthesis of 3-(1,1-dimethoxyethan-2-yl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-p yrazole (2a-b). General procedure: A stirred solution of 4,6,6-trimethoxy-1,1,1-trifluorohex-3-en-2-one (1) (2 mmol) with hydrazine (2 mmol) in 15 mL of dry ethanol was stirred at 80 °C for 4 h (2b) and 20 h (2a). After the reaction time, the solvent was removed under reduced pressure, and the products were dried under vacuum, and isolated as a solid (2a) and an oil (2b) (yields 90-97%).
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31
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59849094304
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note
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2J = 33, C-5), 52.9 (C-7a-b), 46.3 (C-4), 32.2 (C-6).MS: m/z (%) = 305 (20), 95 (97), 75 (100), 47 (47).Anal. Calcd: C, 46.43; H, 4.50; N, 8.33. Found: C, 46.95; H, 4.46; N, 8.49.Melting points and yields of new compounds 2: Compd. [Mp (°C), Yield (%)]: Compound 2a [120-122, 97]; Compound 2b [oil, 90].Melting points and yields of new compounds 2: Compd. [Mp (°C), Yield (%)]: Compound 2a [(120-122), 97]; 2b [(oil), 90].
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32
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59849103922
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note
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Synthesis of 3-(1,1-dimethoxyethan-2-yl)-5-trifluoromethyl-1H-pyrazole (3a-b). General procedure: A solution of 3-(1,1-dimethoxyethan-2-yl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-p yrazole (2a-b) (2.6 mmol) and pyridine (33.8 mmol) in 50 mL of benzene was cooled to 0 °C, and thionyl chloride (16.8 mmol) diluted in 25 mL of benzene was added dropwise over 10 min. The solution was stirred for an additional 30 min, during which time the temperature was allowed to rise to 20 °C. The mixture was then heated under reflux (bath temperature 80 °C) for 1 h, and was then filtered to remove the pyridine hydrochloride at room temperature. The solution was washed twice with water and dried over sodium sulfate. The solvent was evaporated, obtaining dark oils as pure compounds (3a-b). (yields 75-85%).
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33
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59849096139
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note
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3, J = 269 Hz), 113.9 (C-4′), 112.5 (C-4), 102.8 (C-7), 53.4 (C-7a-b), 32.1 (C-6).MS: m/z (%) = 287 (20), 149 (12), 95 (93), 75 (100).Anal. Calcd: C, 49.06; H, 4.12; N, 8.80. Found: C, 48.91; H, 4.22; N, 9.19.Yields of new compounds 3: Compd. [Mp (°C), Yield (%)]: Compound 3a [oil, 75]; Compound 3b [oil, 85].
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34
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59849114510
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note
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Synthesis of 3-(formylmethyl)-5-trifluoromethyl-1H-pyrazole (4a-b). General procedure: A stirred solution of 3-(1,1-dimethoxyethan-2-yl)-5-trifluoromethyl-1H-pyrazole (3a-b) (2 mmol) in 8 mL of chloroform is added to an 4 mL aqueous solution of trifluoroacetic acid (1:1). The solution was stirred for 4 h at 30 °C, and was then washed twice with water and dried over sodium sulfate. The solvent was evaporated, obtaining a yellow solid (4a) or a dark oil (4b), as pure compounds.
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35
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59849091612
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note
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3, J = 269), 113.8 (C-4′), 112.7 (C-4), 42.5 (C-6).MS: m/z (%) = 244 (10), 216 (4), 95 (100).Anal. Calcd: C, 48.54; H, 2.59; N, 10.29. Found: C, 48.63; H, 2.78; N, 10.04.Melting points and yields of new compounds 4: Compd. [Mp (°C), Yield (%)]: Compound 4a [123-124, 55]; Compound 4b [oil, 65].
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36
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59849119937
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note
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3, and filtered. The solvent was evaporated, obtaining a yellow solid (5a) and dark oil (5b). Compound 5a was recrystallized from diethylether and compound 5b was purified by chromatography on silica, using an ethyl acetate and hexane mixture.
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37
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59849104125
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note
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+, 5), 266 (70), 188 (5), 95 (100).Anal. Calcd: C, 44.91; H, 2.40; N, 9.52. Found: C, 44.63; H, 2.51; N, 9.47.Melting points and yields of new compounds 5: Compd. [Mp (°C), Yield (%)]: Compound 5a [128-130, 55]; Compound 5b [oil, 60].
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