High Barium!
So here is the writeup, exactly as it went:
Indole-3-carboxaldehyde, 30ml of MeOH and 25ml Toluene were added to a 500ml RBF. A stir bar was added, and 15,2ml of Methyl-2-chloropropionate was added. 3,6g of Na were dissolved in 40ml of MeOH, and this (slightly yellow) solution was added dropwise to the reaction mixture during ~50 minutes.
On addition the solution became more orangish and all substrate dissolved. The solution was stirred for 2 hours - a relatively small amount of precipiate was seen during this time.
Then 10g NaOH in 50ml were added dropwise. The temp reached ~38°C. 100ml water was added, and the solution was heated to 60-65°C for one our. The solution turned from dark orange to a very deep red.
Then the mixture was poured into a sep funnel and the toluene (which was way darker then the aqueous solution) was drained off. The aqueous layer was acidified with conc. hydrochloric acid. - This caused a lot of orange solids to precipiate out (but no vigorous CO2 evolution was noted, only slight bubbling). This was heated again to 80°C for a good hour.
Then swim wanted to extract the goods with DCM, but he found out that the product wasnt soluble in DCM... so the DCM was drained off again, and the mixture was extracted with ether. - The solubility in ether was also very poor, so swim filtered the crytals and washed them with a lot of cold water.
The ether phase was washed with bicarbonate solution (bicarb-solution turned orange too!), then with water, and finally the solvent was removed on the rotary evaporator.
The combined crystals were dried, and then recrystallized from ~80ml of IPA to yield a pale orange solid with the same rentention time on HPLC as Indole-3-carboxaldehyde (eluent: methanole, column: nucleosil 5C-18), and also the same melting point of about ~195°C.
Does anybee have some ideas what went wrong?
I dont wanna waste any more precoursor until i know what caused the failure....
...everything looked that good during the reaction!
best wishes,
xicori