If you have access to org chem journals look those references:
in
Post 427106
(Chimimanie: "On tryptophol", Tryptamine Chemistry)244a,b for 5-MeO-tryptophol
681 for the alpha-methyl derivative as well as 739
687 and 688
and 231 and 673 for the 5-benzyloxyderivative
look those posts (As well as the threads which contain them!)
Post 218769
(foxy2: "Tryptophol Synthesis", Tryptamine Chemistry) just use 4-MeO-phenylhydrazine instead (avaiable from oversea suppliers), or the synth is at rhodium's site.
Post 407891
(Rhodium: "o-Iodoaniline + Butynol -> Tryptophol -> DMT", Tryptamine Chemistry) the mesylate swap, you could use tosylate, but maybee side reaction could occur due to solvent effects
Post 197106
(Lilienthal: "Re: looked up some nice ref's", Tryptamine Chemistry) (Yes PBr3 could bee used instead)
Post 412787
(Chimimanie: "N-Methylisopropylamine for MIPT and the like", Tryptamine Chemistry) could give you some hints.
And IMHO the best method to obtain 5-Meo-tryptophol is from the 4-MeO-phenylhydrazine and dihydrofuran (or another furan derivative like foxy described) , with a little dash of ZnCl2. This method bypass the Na/EtOH or LAH reduction, which are tedious and use suspicious chemicals.
Otherwise plenty routes are of course avaiable, the indoleglyoxyl chloride one (from 5-MeO-indole + oxalyl chloride then Diisopropylamine work as well (see Journal of Heterocyclic Chemistry (1983), 20(4), 1031-6 for a ref on 5,6-methylenedioxy indole)) for instance, or the various fisher indole synthesis see all the thread
Post 335108
(Rhodium: "Fisher Tryptamine Synthesis - is this right?", Tryptamine Chemistry).
And if you understand french, the 5-methoxy-3-indolyl-N,N-diisopropylglyoxylamine is cited and prepared in Bull. Soc. Chim. France (1965), (5), 1411-17.
This is a part of the abstract of that text:
In an alternative method, 5-methoxyindolyl-2-carboxylic acid (IV) was decarboxylated in 73% yield by heating at 230° in a Peligot tube until evolution of gas was complete. Alternatively, a mixt. of 70 g. IV, 150 cc. quinoline, 8 g. Cu(OAc)2, and 4 g. powd. Cu was refluxed 3 hrs. and extd. with Et2O. The org. ext. was washed 4 times with 2N HCl, then H2O, dried, and distd. to give 72% 5-methoxyindole (V), b0.2 125-30°, m. 57°. A soln. of 55 g. (COCl)2 in 60 cc. Et2O was added to a soln. (cooled to 0°) of 50 g.
V in 600 cc. dry Et2O. The mixt. was stirred 1 hr. and filtered to give 85 g. 5-methoxyindolyl-3-glyoxylyl chloride (VI). A mixt. of 12 g. VI, 10 cc. 40% aq. Me2NH, and 200 cc. ice water was stirred 4 hrs. at 0° to give 87% 5-methoxy-3-indolyl N,N-dimethylglyoxylamine (VII, R1 = R2 = Me) (VIII), m. 221°
Redn. of VIII by LiAlH4 in tetrahydrofuran as described previously gave 81% 5-methoxy-3-(2-dimethylaminoethyl)indole (IX, R1 = R2 = Me), the hydrochloride of which m. 146°. R1, R2 5-Methoxy, % yield, M. p.; Et, Et, 80.5, 160°; Pr, Pr, 91, 150°; iso-Pr, iso-Pr, 75.5, 225°
So 5-MeO-DipT is avaiable in 75% yield from the reduction of the glyoxyl amide which is avaible from 5-MeO-indole and oxalyl chloride followed by reaction with aqueous diisoproplyamine. 5-MeO-indole is avaiable from the 5-methoxyindolyl-2-carboxylic acid which itself should be avaible from the 4-MeO-phenylhydrazine through a Japp-Klingemann reaction. Alternatively the 5-MeO-indole is avaiable also from air oxydation of beta-ethylamino-hydroquinone, see ref [8] of
Post 407846
(Chimimanie: "Proposed method (1) for 2C-H", Novel Discourse) or by other means I dont know by heart.
But I prefer to do one fisher synthesis and no reduction, starting from scratch I really think the tryptophol road is the best.
UTFSE and you should also read Heterocyclic Compounds, Indoles, Part 1,2 and 3, Houlihan, Wiley
peace
