Boron trifluoride etherate → HCID 66670094, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 42 (8.6 g, 22 mmol) in DCM (80 ml) was cooled to −78° C. To this solution was slowly added boron trifluoride etherate (2.8 mL, 22 mmol) followed by the addition of 1M DIBALH in DCM (60 mL). The solution was stirred at −78° C. for 1 h. The reaction mixture was then treated with EtOAc and stirred for 30 min. The reaction mixture was allowed to warm to −5° C. The reaction was quenched by the dropwise addition of 1M HCl. The mixture was diluted with DCM and H2O and the layers were separated. The aqueous layer was extracted with DCM. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated to afford 8.5 g of 43 as a light yellow oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ5.70 (m, 1H), 5.59-5.55 (m, 1H), 4.16-4.13 (m, 2H), 4.05 (m, 2H), 3.72-3.35 (m, 4H), 1.95-1.88 (m, 2H), 1.77-1.67 (m, 2H), 1.48-1.44 (m, 9H), 0.88 (s, 9H), 0.08-0.03 (m, 6H) ppm.

Provenance & Evidence