Chapter 54: Chapter 52 Beginning Synthesis!
"Old Qiu, what’s happening?"
As soon as Xu Yun returned to the lab, he asked Qiu Sheng, who was holding a test tube:
"It’s been just over an hour, right? The substitution reaction is completed already?"
"Exactly, let me put this down first."
Qiu Sheng carefully placed the test tube down, walked over to another table to pick up a paper report, and handed it to Xu Yun:
"To be precise, it was one hour and twenty-seven minutes. The activity of 5-epoxy-1-hexadecene seems much higher than we anticipated."
Xu Yun glanced at the report and nodded:
"This kind of curve... It seems to be an issue with the temperature setting, probably related to when I asked Xiaozhao to increase the temperature.
Old Qiu, my expertise isn’t in chemistry; does 5-epoxy-1-hexadecene have that much difference in activity between 180 degrees and 170 degrees?"
Qiu Sheng pondered for a while, then shook his head:
"I’m familiar with 5-epoxy-1-dodecene, but hexadecene... seems not well understood domestically.
and 170 degree environments are fairly common, but adding a substitution reaction complicates things; after all, carbynes... are more studied now in material science."
Xu Yun pondered and nodded, falling silent.
Carbynes refer to chains formed by carbon atoms clustering together, linked via double bonds or alternating single and triple bonds.
Carbynes have been shown to be more than 200 times stronger than steel, with twice the tensile strength of graphene, considered the toughest material on Earth, 40 times stronger than diamonds.
It was proposed in 1885, but it wasn’t until April 21, 2016, that the University of Vienna created a carbon chain composed of 6400 carbon atoms.
From a mass production perspective, it is indeed a relatively new product.
Epoxy carbyne is somewhat more complex, and Xu Yun didn’t anticipate it as a final product.
The introduction of this substance is mainly intended for the epoxy end alkyne to react with 1-bromo-2-pentyne under copper iodide catalysis to form epoxy diacetylene.
Finally, hydrogenation catalyzed by nickel acetate/borohydride sodium produces the target pheromone (3Z, 6Z, 9S, 10R)-9,10-epoxy-3,6-docosaene.
Thus, 5-epoxy-1-hexadecene is an intermediate in the entire reaction; Xu Yun’s initial thought was merely hoping it could serve a stabilizing bridging role.
But given the current situation...
This thing seems to exhibit some reactive chemical properties under specific circumstances?
Xu Yun silently noted this situation in his mind, planning to consult more knowledgeable colleagues, while telling Qiu Sheng:
"Alright, let’s continue."
Qiu Sheng nodded repeatedly, followed Xu Yun back to work.
Perhaps after lunch, compared to the relatively dry cooperation in the morning, the afternoon project group worked smoothly like clockwork.
After a whole night of working overtime, the group finally synthesized the target pheromone in the early morning, nearly ten hours ahead of Xu Yun’s original estimate.
......
A night passed without incident.
At 1:30 PM the next afternoon, Xu Yun stood at the main workstation once again.
"Fellow students."
He glanced around, reminiscing that the last time these six gathered felt like just yesterday:
"Thanks to everyone’s tireless efforts yesterday, we’ve cleared the first hurdle of this project. No need for further ado, let’s feast tonight!"
"Clap clap clap——"
As soon as he finished speaking, Tang Yiqiu and others began applauding.
Xu Yun paused before continuing:
"Additionally, from today, we’re starting the synthesis of both pheromone and Imidacloprid, which mainly involves two steps:
First is through an asymmetric orientation given to CH3 for cyclization, and second is the synthesis of new substances.
The target pheromone structure we’ve synthesized is extremely complex, so it’s uncertain if we can precisely remove a CH3 for cyclization. Your collaboration is essential for great results!
Alright, that’s all for now; let’s start the experiment!"
With that, he waved his hand, and everyone returned to their stations.
Xu Yun moved to the main workstation, personally taking charge of the key steps.
"Xiaotang."
Xu Yun seriously made preparations, while telling Tang Yiqiu:
"Start by adding protective argon!"
"Understood!"
After the argon was added, Xu Yun began adding 50 mol of anhydrous LTHF and 20 g hexamethylphosphoramide to a 250 mL Schlenk flask, stirring to dissolve.
Upon completion, he lowered the reaction system’s temperature to -78℃, added 2.52 g of propargyl alcohol, and used a syringe to gradually add n-butyllithium, then raised the temperature to -30℃.
After three more hours, the stirring reaction fully occurred.
"Xiaotang, prepare 22.50 mmol of 1-bromoundecane!"
Meanwhile.
In the invisible microscopic domain, some peculiar reactions quietly occurred.
LTHF, technically should be called LT-HF.
The former stands for low temperature, while HF is hydrogen fluoride.
LTHF and hexamethylphosphoramide are like adolescent boys and girls, fond of each other but afraid to express it, stalling, only progressing to borrowing an eraser.
At this point, the bold 1-bromoundecane emerges.
It behaves like a typical street jerk from novels, pinning delicate hexamethylphosphoramide against the wall one afternoon.
"Don’t come here, let go!"
"Hehehe, little sister, would you like to take a ride?"
1-bromoundecane approached hexamethylphosphoramide, cornered her, and even grabbed her hand.
"Let go of me!"
At this moment, the pure-hearted boy LTHF arrives. He first picked up a stone from the ground (propargyl alcohol decomposed a hydrogen), and threw it hard at 1-bromoundecane.
The stone hit 1-bromoundecane heavily, spilling bright red droplets (three carbons).
While 1-bromoundecane clutched his head in agony, LTHF grabbed hexamethylphosphoramide and fled.
Arriving at a deserted alley, hexamethylphosphoramide looked up with tearful eyes at LTHF:
"Why did you save me?"
LTHF scratched the back of his head, eyes wandering:
"Because... because..."
Muttering for a while, he still lacked the courage to say ’I like you.’
At that moment, he felt a soft moistness on his lips.
His eyes widened with shock, staring ahead, meeting hexamethylphosphoramide’s loving eyes.
Hexamethylphosphoramide stretched out three nitrogen-hands, hugging LTHF, her second mouth of oxygen softly said:
"LTHF, I like you..."
"Pop!"
Meanwhile, in the lab, Xu Yun clapped his hands together:
"Perfect, the reaction is complete!"