3
$\begingroup$

Instead of using oxalyl chloride and DMF then $\ce{AlCl3}$, could $\ce{SOCl2}$ followed by $\ce{AlCl3}$ been used to achieve the same result? If yes, is one pathway preferred over the other and why?

Reaction

This reaction comes from Simmons, E. M.; Sarpong, R. Ga(III)-Catalyzed Cycloisomerization Strategy for the Synthesis of Icetexane Diterpenoids:  Total Synthesis of (±)-Salviasperanol. Org. Lett. 2006, 8 (13), 2883–2886.

$\endgroup$

1 Answer 1

3
$\begingroup$

They should both work. I would use oxalyl chloride with a solvent like DCM. DMF should act as a catalyst here for the acid chloride formation. (I don't have access to the paper but this is most likely what they have done) The oxalyl chloride reaction is maybe easier to work-up although I don't think there is a big difference when working in lab scale. In this case you can skip work-up (assuming you have used DCM as solvent and 1-2 equivalents of oxalyl chloride) and just add $\ce{AlCl3}$ for the cyclisation step.

EDIT: You can read the experimental in the supporting info -page S7

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.