Preparation method of optically active 4-phenylthio-2-butanol
An optically active, phenylthio-based technology, applied in the field of preparation of optically active 4-phenylthio-2-butanol compounds, can solve the problems of many by-products and difficult purification, and achieve less by-products, easy purification, The effect of simple and easy process
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Embodiment 1
[0039] Preparation of R-4-phenylthio-2-butanol
[0040] Dissolve 10.0 g of sulfide anisole in 136 ml of tetrahydrofuran, add 34 ml of hexamethylphosphoramide, cool to -78°C, add 54 ml of 1.6M n-hexane solution of butyllithium, stir for 0.5 hours, then add dropwise R -4.9 g of propylene oxide in 10 ml of THF, stirred at -78°C for 2 hours, then poured the reaction solution into ice water, adjusted the pH to 6 with hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated to obtain 14.4 gram of light yellow oily substance, the low boiler was evaporated under reduced pressure, and the residue was 12.8 grams. After purification by silica gel column, 12.6 grams of the product were obtained, with a yield of 85.7%.
[0041] (α) D20: -20.3o (C=3.6, CHCl3)
[0042] NMR (CDCl3) 1.18 (3H, d), 1.53-1.95 (2H, m), 3.00 (2H, m), 3.95 (1H, m), 7.08-7.35 (5H, m).
Embodiment 2
[0044] Preparation of S-4-phenylthio-2-butanol:
[0045] Dissolve 5.0 g of sulfide anisole in 60 ml of tetrahydrofuran, add 15 ml of hexamethylphosphoramide, cool to -78°C, add 17 ml of 1.6M n-hexane solution of butyllithium, stir for 0.5 hours, add dropwise S - 2.5 grams of propylene oxide in 10 milliliters of tetrahydrofuran solution, after stirring for 2 hours, operate according to Example 1 to obtain 6.2 grams of product with a yield of 84.5%.
[0046] (α) D20: +19.8o (C=3.6, CHCl3)
[0047] NMR (CDCl3) 1.18 (3H, d), 1.52-1.95 (2H, m), 3.01 (2H, m), 3.97 (1H, m), 7.10-7.36 (5H, m).
Embodiment 3
[0049] Preparation of R-4-phenylthio-2-butanol
[0050] Chloromethyl phenylene sulfide 3.17 g, magnesium chips 0.5 g, tetrahydrofuran 50 ml, add small grains of iodine, heat to reflux, after the reaction is initiated, reflux until magnesium chips disappear, after reflux for 0.5 hours, cool to -5 ° C, drop 1.5 A solution of R-propylene oxide in 5 mL THF. After dropping, keep stirring for 1 hour, then stir at room temperature for 0.5 hour, add saturated ammonium chloride solution, extract with ethyl acetate, and then operate according to Example 1 to obtain 1.9 g of the product, with a yield of 52.2%. NMR (CDCl3) 1.17 (3H, d), 1.52-1.97 (2H, m), 3.00 (2H, m), 3.96 (1H, m), 7.08-7.36 (5H, m).
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