Hydrogen Peroxide → HCID 59315611, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-methyl-2-butene (204 mmol, 21.68 mL) dissolved in tetrahydrofuran (150 mL) was cooled in a salt-ice bath and 1M boran-THF complex (34.1 mmol, 34.1 mL) was slowly added maintaining the temperature below 0° C. Upon complete addition the reaction mixture was left to stir for 10 minutes at 0° C. and then a tetrahydrofuran solution of (S)-tert-butyl 1-(2-bromophenyl)but-3-enylcarbamate (compound 4; 68.1 mmol, 22.23 g) was added slowly maintaining the temperature below 5° C. Once the addition was complete the cooling bath was removed and the temperature allowed to warm to room temperature and left to stir for 60 minutes. After 60 minutes the reaction mixture was cooled back to 0° C. and 4N sodium hydroxide (80 mmol, 20 mL) was slowly added at below 5° C. and this was followed by 27.5% aqueous hydrogen peroxide solution (68.1 mmol, 20 mL) keeping the temperature below 5° C., once the addition was complete the cooling bath was removed and the temperature allowed to warm to ambient temperature and left to stir overnight. The reaction mixture was diluted with ether (500 mL) then water (500 mL), the aqueous was phase separated and the aqueous re-extracted with ether (3×500 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give an white solid that was taken up in methylene chloride an loaded on to a silica pad and eluted with 40% ethyl acetate-heptane to give (S)-tert-butyl 1-(2-bromophenyl)-4-hydroxybutylcarbamate (8.08 g), MS (ES): m/z [M+H]+ 344 and 346.

Provenance & Evidence