[Kunshirostorm]

if fisher indole synthesis works, phenylhydrazine with succinaldehyde will make indole-3-acetaldehyde

i don't know if it works this way so if someone can answer this question it would be great

[rolnor]

I think the hydrazine will attack both ends of the succinic aldehyde, probably form a ring.
You could protect one aldehyde group as a 1,3-dithiane, this can give the indole but you get to unprotect it so 2 more steps. I think you can buy this protected succinic aldehyde.

[Kunshirostorm]

I think the hydrazine will attack both ends of the succinic aldehyde, probably form a ring.
You could protect one aldehyde group as a 1,3-dithiane, this can give the indole but you get to unprotect it so 2 more steps. I think you can buy this protected succinic aldehyde.

but do the Dithiane protect both side of succinaldehyde, because i whant 1,3-Dithiane-2-propanal so that i form indole,  is there a way to synthetise it or do i need to buy 1,3-Dithiane-2-propanal

I have another idea, can i take 4-hydroxybutanal, mix with phenylhydrazine to make Tryptophol. Then i just need to oxyde it to get indole-3-acetaldehyde

[rolnor]

I think the hydrazine will attack both ends of the succinic aldehyde, probably form a ring.
You could protect one aldehyde group as a 1,3-dithiane, this can give the indole but you get to unprotect it so 2 more steps. I think you can buy this protected succinic aldehyde.

but do the Dithiane protect both side of succinaldehyde, because i whant 1,3-Dithiane-2-propanal so that i form indole,  is there a way to synthetise it or do i need to buy 1,3-Dithiane-2-propanal

No, the dithiane will form a mixture of mono and di-protected material, you are correct.
I think your second method would work. I have a feeling that there must be a litterature method how to make this indole aldehyde?

I have another idea, can i take 4-hydroxybutanal, mix with phenylhydrazine to make Tryptophol. Then i just need to oxyde it to get indole-3-acetaldehyde