[wildfyr]

Ha well that silver triflate was never gonna be cheap!

[zarhym]

Ha well that silver triflate was never gonna be cheap!

Redesign the whole scheme means significant amount of time and work.

Silver triflate is about $1/g in China. I purchased this chemical directly from manufacturer.
160RMB for 25g Silver triflate, 16% tax included.



 

[rolnor]

Realy cheap, the price of silvermetal itself is higher? It would be interesting to se the rest of your synthesis scheme but as you say, it will be a lot of work to remake everything even if we can give you suggestions here in the forum.

[zarhym]

Realy cheap, the price of silvermetal itself is higher? It would be interesting to se the rest of your synthesis scheme but as you say, it will be a lot of work to remake everything even if we can give you suggestions here in the forum.

Here it is.
This project was attempted and failed in etherificaion in other CRO company.
My client suggest this approach may be feasible since there there is some record in reaxys and scifinder database that amine can couple with this "benzylbromide". I did some literature research and consulted a couple of experienced chemists. All of us agreed that this approach may be possible.

My total budget for this project is about 22000 RMB (less than USD 4000), while the labor cost in China is about 8000RMB/month (USD 1200/month). It is ok for us to spend small amount of money and time to test first couple reactions. But if we change the scheme, there will be almost no reference available and the risk is significant increased. The decision was made based on the balance of risk and profits.

This project may be another story if I am funded by NSFC. Unfortunately I am runing a very small CRO company funded by myself.

[OrganicDan96]

just an idea, Keep the alcohol in high dilution to prevent intermolecular anhydride ring opening,  use a non nucleophillic base (DBU might work but is expensive). use a very large excess of alkyl halide.

[rolnor]

I feel that the furandione is very difficult to work with, the double bond can give Mickael-addition reaction even if you can transform the anhydride to dimethyl ester.
You have many sensitive groups present in the same molecule and you need time and/or luck to pull this off.

[kriggy]

Why dont you first condense hydrazino-pyridine with the anhydride and then form the ether?

[zarhym]

Why dont you first condense hydrazino-pyridine with the anhydride and then form the ether?

I know. I'd like to do that if I have more financial support.

[kriggy]

Why dont you first condense hydrazino-pyridine with the anhydride and then form the ether?

I know. I'd like to do that if I have more financial support.

Wait what? You just intrchange two steps using the compounds you are already using / going to use