Process for preparing carotenoid polyene chain compounds and intermediates for preparing same
A compound, monoxide technology, applied in the field of lycopene, can solve problems such as not easy to form double bonds
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Embodiment 1
[0066] Example 1: 2-Methyl-4-phenylthio-2-butenyl-1-ol
[0067] Dissolve isoprene monoxide (0.30 ml, 3.1 mmol) in N,N-dimethylformamide (DMF) (7 ml), and add cuprous iodide (CuI) to it at 0°C (15 mg, 0.08 mmol) and thiophenol (PhSH) (0.33 mL, 3.2 mmol). The final reaction mixture was stirred at the same temperature for about 6 hours.
[0068] When the reaction was complete, the reaction mixture was diluted with ether, then washed three times with 1M-HCl (10 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2-methyl-4-phenylthio-2-butenyl-1-ol (0.52 g, 2.7 mmol ) (Yield: 87%). according to 1 According to the analysis data of H-NMR and gas chromatography, the ratio of trans-type and cis-type double bonds is not less than 6:1.
[0069] 1 H-NMR: trans δ 1.56(s, 3H), 2.38(br s, 1H), 3.55(d, 2H, J=7.7Hz), 3.92(s, 2H), 5.54(t, 1...
Embodiment 2
[0072] Example 2: 4-bromo-3-methyl-2-butenylphenyl sulfide
[0073] Slowly add ether (80 ml), PBr 3 (16.5 g, 61 mmol). The final reacted mixture was stirred at 0°C for about 1 hour. When the reaction was completed, the reaction mixture was diluted with ether, washed with distilled water, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-bromo-3-methyl-2-butenylphenyl sulfide (26.8 g, 104 mmol) ( Yield: 85%).
[0074] 1 H-NMR: trans δ1.64(s, 3H), 3.51(d, 2H, J=7.7Hz), 3.92(s, 2H), 5.72(t, 1H, J=7.7Hz), 7.18~7.41( m, 5H); cis δ1.85(s, 3H), 3.56(d, 2H, J=7.9Hz), 3.79(s, 2H), 5.52(t, 1H, J=7.9Hz), 7.18~7.41 (m, 5H).
[0075] 13 C-NMR: δ 14.7, 32.4, 40.4, 125.9, 126.7, 128.9, 130.9, 135.4, 135.5.
Embodiment 3-1
[0076] Example 3-1: 5-Benzenesulfonyl-1-phenylthio-3,7,11-trimethyl-2,6,10-dodecatriene
[0077] Geranyl sulfone (28.7 g, 103 mmol) was dissolved in THF (150 ml), and then n-BuLi (1.6M hexane-solvent solution / 64 ml, 103 mmol) was slowly added thereto at 0°C . The final reacted mixture was stirred for about 20 minutes. 4-Bromo-3-methyl-2-butenylphenylsulfide (29.1 g, 113 mmol) was added to the reaction mixture. The reaction temperature was slowly raised to room temperature, and the mixture was stirred at the same temperature for about 11 hours.
[0078] 100 mL of ether was added to the reaction mixture, and the final mixture was washed well with 1M-HCl aqueous solution (20 mL×2) and distilled water (30 mL). The mixture was dried over anhydrous sodium sulfate and filtered.
[0079] The filtrate was concentrated by distillation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 5-benzenesulfonyl-1-phenylthio-3,7,11-trimethyl-2,6...
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