Sodium Chloride → HCID 12967236, compound

Participants

Reaction Conditions

Reaction Steps

2.16 g (7.77 mmol) of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (compound (5)) was added to a mixed solvent of 20 ml of THF and 2 ml of H2O, followed by stirring at 0° C. To this solution, 1.54 g (8.65 mmol) of NBS was added, and while gradually raising the temperature to room temperature, stirring was continued overnight. Then, 140 mg (0.787 mmol) of NBS was further added, followed by stirring for 6 hours. The reaction mixture was put into a saturated sodium chloride aqueous solution and extracted with ethyl acetate. The extract layer was washed sequentially with an aqueous sodium thiosulfate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrated product was crystallized from a mixed solvent of ethyl acetate and hexane to obtain 1.323 g of 2-(4-bromo-3-methoxyphenyl)-3-t-butyl-3-hydroxy-4,4-dimethyl-2,3,4,5-tetrahydrofuran (compound (6)) in a yield of 47.7%.

Provenance & Evidence