Sodium Chloride → HCID 12967236, compound

Participants

Reaction Conditions

Reaction Steps

Adding 2.16 g (7.77 mmol) of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (Compound [50]) to the mixture of 20 ml of THF and 2 ml of H2O, the mixture was stirred at the temperature of 0° C. After adding 1.54 g (8.65 mmol) of NBS, the mixture was stirred over night with increasing the temperature to a room temperature gradually, 140 mg (0.787 mmol) of NBS was added and the mixture was stirred for 6 hours. The mixture was added to saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was washed with a solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride in this order, then dried with magnesium sulfate anhydride and concentrated. The concentrate was crystallized with the mixture of hexane and ethyl acetate 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 [51]). Yield 47.7%

Provenance & Evidence