Tetrahydrofuran → (9RS)-(1R*,8S*)-Tricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-ol

Participants

Reaction Steps

A solution of 15.8 g of tricyclo[6.2.2.02,7]dodeca-2,4,6,9-tetraene in 42 mL of THF was added to 82 mL of 1M BH3 in THF at 0° C. The reaction mixture was stirred overnight while the temperature reached rt. The reaction was quenched by addition of 40 mL of 0.3N NaOH solution followed by 134 mL of a 35% H2O2 solution. The mixture was extracted with Et2O, washed with H2O, dried over MgSO4 and concentrated in vacuo to obtain 17.7 g of the desired compound as yellow oil.

Provenance & Evidence