Thank you always for the great videos all the way from Japan! Can you tell me why the secondary alcohol dont go through appel reaction in the second step?
Hi. The reaction conditions are available in the SI of the reference paper. I see now that the acidic proton of the terminal alkyne may be problematic; however the reagent is commercially available. To ethynylmagnesium bromide (200 mL, 0.50 M in THF, 2.00 equiv.) in THF was added CuCl (2.48 g, 25.0 mmol, 0.500 equiv.). The mixture was stirred for 15 min under argon before substrate (8.74 g, 50.0 mmol, 1.00 equiv.) in THF (25 mL) was added. The reaction was stirred at 50 °C for 6 h until it was quenched with saturated NH4Cl (50 mL) and H2O (200 mL).
Thanks for including structures of the intermediates
Very nice explanation sir , can you explain recent total synthesis of terpenoids
Thank you always for the great videos all the way from Japan! Can you tell me why the secondary alcohol dont go through appel reaction in the second step?
Thank you. Using 1.05 eq. of iodide, I assume the reaction takes place mainly with the most exposed primary alcohol.
Grignard Reaction does not work in presence of alkynes (tested), is there anything specific you did to make it work?
Hi. The reaction conditions are available in the SI of the reference paper. I see now that the acidic proton of the terminal alkyne may be problematic; however the reagent is commercially available.
To ethynylmagnesium bromide (200 mL, 0.50 M in THF, 2.00 equiv.) in THF was added CuCl (2.48 g, 25.0 mmol, 0.500 equiv.). The mixture was stirred for 15 min under argon before substrate (8.74 g, 50.0 mmol, 1.00 equiv.) in THF (25 mL) was added. The reaction was stirred at 50 °C for 6 h until it was quenched with saturated NH4Cl (50 mL) and H2O (200 mL).