Mildew Moulda, Huffin Etherb, Burnie Urethraa
Abstract: An elegant procedure for the progression towards the total synthesis of Impracticatechol is presented. The importance of this work is such that we reserve the right for further miscommunications in this field.
Specific: Enthrawaling. A compulsive read and page turner − Penury Times
Impracticatechol (Figure 1) was first isolated from the nightmares of Holden Captiva, a student of the late Winnie Bago, a pioneering organic chemist at the Rural University of Penury Bridge. This compound has been found to marginally improve the artistic tendencies of laboratory toads. However, this extremely promising biological activity is marred by potent cytotoxicity, excitotoxity, genotoxicity, mutagenicity, carcinogenicity and teterogenicity. It is perhaps for these reasons, or its incomprehensively complicated structure, that no intelligent person in their right mind would want to make it, so we did.
Impracticatechol was long deemed too mentally tormenting to attempt any form of synthesis until recently when our group published progress on the topic.1 On the back of this work, we made the interesting observation that the key to finishing the total synthesis was in fact starting it. With this in mind, we present the first partial total synthesis of impracticatechol.
Figure 1. Impracticatechol
Results and Discussion
We predicted that key to forming the overwhelmingly complex structure of impracticatechol was forming all the bonds in the right places. With a sinking feeling in our hearts, we began (and ended) our synthesis with a Friedel-Crafts acylation of catechol. Many months of tireless work and microwave pizza dinners passed until, after arduous optimisation and the forgoing of mental wellbeing, our optimal reaction conditions yielded functionalised catechol 1 in 6.3% yield (scheme 1). This result was met with joyous celebration down the Penury Bridge Tavern and a two-day hangover.3 This pioneering pathway offers the possibility to attempt the second step, a methylmagnesium bromide addition to the ketone, which, if successful will be the topic of a future miscommunication. The success of the first step is predicted to open a floodgate of research into not only impracticatechol, but other supernatural products such as inconceivacatechol and misseratechol.
Scheme 1: Progression towards the total synthesis of impracticatechol.
Experimental
Representative procedure: A poorly dried, cracked 500 mL two neck flask was sealed with Duct Tape and Blu Tack before being evacuated via human diaphragm and plastic hosing (362 torr). The flask was refilled with N2 and AlCl3 (1 equiv.) and dry DMF4 (40 mL) was added. The mixture was heated to 40 °C before catechol (1 equiv.) and 3-hydroxypropanoyl chloride (36 equiv.) were added. The reaction was heated to 90 °C and then a stir bar was added.5 The ‘burnt marshmallow’ coloured solution was stirred for 38 hours before tap water (50 mL) and ethyl acetate (40 mL) was added. The solution was then inadvertently decanted onto a polyvinylchloride fume hood and absorbed into, then extracted from, 3 sheets of paper towel (at this point the supervisor (principal investigator) was informed that results looked “promising”). The phases were separated and the aqueous phase was extracted with ethyl acetate (3 x 40 mL), dried (NasSO4) and filtered. The solution was then added to 2.4 L of H2O maintained at 35 °C. The aqueous phase was then painfully extracted with ethyl acetate (37 x 30 mL) then washed with sea water (30 mL). The combined organic phases were scolded (verbally), dried (Na) and filtered (hastily). The solvent was removed, and the flask let to stand open to air at r.t. for several weeks. The crude tar was purified by trituration over DMSO, recrystallisation from ethanol and subjected to column chromatography (10% ethyl acetate/hexanes − 40% methanol/DCM) to give catechol 1 (9 mg, 6.3% yield) and mental exhaustion (insomnia, 93% yield). Naturally, catechol 1 was contaminated with trace triphenylphosphine oxide so a small sample was prepared for spectroscopic analysis via preparative TLC and Adobe Photoshop. IR: See ref 2 1H NMR: δ 1.1−7.9 (m, 10 H) ppm. C13 NMR: forgot.
Conclusions
In conclusion we present the first step in a 42 step envisioned sequence towards the total synthesis of impracticatechol. Future research will focus on the remaining 41 step sequence which at the current rate will be completed early next century.
About the Authors
Mould Mildew is an undergraduate student at the Rural University of Penury Bridge. She plans to fake her own death to avoid paying her tuition debt. Huffin Ether voluntarily distils solvents upon request. Burnie Urethra received Green, Amber and Red level Laboratory and Workshop Induction Certificates at the beginning of 2021.
Author Contributions
Mould performed the reaction seen herein. Her yearlong commitment to the reaction optimisation and busking performances at Penury Bridge Clocktower to raise funds were vital in the success of this work. Huffin works at the local Bunnings and is the provider for many of solvents and chemicals used at the Rural University of Penury Bridge. Burnie Urethra tirelessly tracked down the names and addresses of the three reviewers whom emphatically did not support the publishing of this work − they changed their minds.
Conflicts of Interest
Burnie is severely conflicted in almost all facets of his life. Huffin apparently has nothing to declare as long as no one goes in his greenhouse.
Acknowledgements
We would like to say fuck u to all the haters out there sum days it gets tuff you know but yeah just fuck the haters aye. Also FYI haters I’d like to see you all try do this at least we are out here having a crack and now we are published in a proper journal so yeah I reckon yous can all get fucked especially Nature and Science yous wouldn’t know a good manuscript if it was lodged up your ass.
Notes and references
1. B. Urethra. Starting to think about the possibility of progressing towards the total synthesis of impracticatechol perhaps. J. Hopes N. Dreams. 2021, 4, 6743
2 . Y. Bother. The IR spectrum of carbon dioxide. J. Cutt. Corn. 1987, 2, 30.
3. S. Beak. Professor Charged Over Booze-Fuelled University Damage. Penury Times. 13/5/21.
4. DMF was dried by decanting over molecular sieves and storing in a PVC container under a tarpaulin.
5. Forgot to add stir bar to begin with
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