Process for the preparation of chiral 2-hydroxymethyl-1,4-benzodioxane compound
A technology of benzodioxane and hydroxymethyl, which is applied in the field of preparing chiral 2-hydroxymethyl-1, can solve the problems of low optical purity and low economy, and achieve the effect of improving the total yield
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example 1
[0054] 10 g (0.1081 mol, 1.0 equivalent) of (R)-epichlorohydrin was dissolved in 18 ml of ethyl acetate, and 21.436 g (0.1946 mol, 1.8 equivalent) of catechol were added thereto. To this solution was added 1.74 ml (0.0216 mol, 0.2 equivalent) of pyridine, and stirred at 40° C. for 2 days. 2M sulfuric acid solution was added to the reaction mixture to adjust the pH to 4-5. After washing with water, the solvent was removed under reduced pressure. The obtained crude product was dissolved in 23ml of methanol, and 233ml (0.2594mol, 2.4eq) of 2M NaOH was added dropwise at 0°C for 1.5 hours. After stirring for 2.5 hours, the reaction mixture was extracted with dichloromethane. The extract was washed successively with 2M aqueous NaOH solution and water, dried over anhydrous magnesium sulfate and filtered. The solvent was removed from the mother liquor under reduced pressure to yield 12.124 g (68%, 99.4% ee) of (R)-2-hydroxymethyl-1,4-benzodioxane.
[0055] The optical purity (%ee)...
example 2
[0057]10 g (0.1081 mol, 1.0 equivalent) of (R)-epichlorohydrin was dissolved in 18 ml of acetone, and 21.436 g (0.1946 mol, 1.8 equivalent) of catechol were added thereto. To this solution was added 1.74 ml (0.0216 mol, 0.2 equivalent) of pyridine, and stirred at 40° C. for 2 days. The solvent was removed under reduced pressure. The obtained crude product was dissolved in 23ml of methanol, and 233ml (0.2594mol, 2.4eq) of 2M NaOH was added dropwise at 0°C for 1.5 hours. After stirring for 2.5 hours, the reaction mixture was extracted with dichloromethane. The extract was washed successively with 2M aqueous NaOH solution and water, dried over anhydrous magnesium sulfate and filtered. The solvent was removed from the mother liquor under reduced pressure to afford 11.045 g (61%, 99.2% ee) of (R)-2-hydroxymethyl-1,4-benzodioxane.
example 3
[0059] 10 g (0.1081 mol, 1.0 equivalent) of (R)-epichlorohydrin was dissolved in 18 ml of ethyl acetate, and 21.436 g (0.1946 mol, 1.8 equivalent) of catechol were added thereto. To this solution was added 0.87 ml (0.0108 mol, 0.1 equivalent) of pyridine, and stirred at 40° C. for 3 days. 2M sulfuric acid solution was added to the reaction mixture to adjust the pH to 4-5. After washing with water, the solvent was removed under reduced pressure. The obtained crude product was dissolved in 23ml of methanol, and 233ml (0.2594mol, 2.4eq) of 2M NaOH was added dropwise at 0°C for 1.5 hours. After stirring for 2.5 hours, the reaction mixture was extracted with dichloromethane. The extract was washed successively with 2M aqueous NaOH solution and water, dried over anhydrous magnesium sulfate and filtered. The solvent was removed from the mother liquor under reduced pressure to afford 9.551 g (53%, 99.3% ee) of (R)-2-hydroxymethyl-1,4-benzodioxane.
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