Almost neopentyl moiety still 98% yield in SN-2 reaction

This one is in memoriam of my old master Prof. Dr. Hans Wynberg (Dutch Hans Wijnberg, but he liked to make it more international like with ij an y so Hans Wynberg):

(1922 – 2011) RIP Hans was role model for the film “Inglorious Bastards” he was during WW2 in the OSS, and a Jewish avenging angel spy in Nazi occupied France, OSS was the forerunner of the CIA.

Hans learned me some tricks!

Hans told me way back around 1985 already I should publish my findings on the 5,7-di(1-butoxy-3-on)-2,3-dimethylbenzofurane syntheses, because the yield was abnormally high (98% H-NMR yield, we call that quantitative). As Hans said: “This is interesting because the used reagent 2 chloro-3-butanone is almost NEOPENTYL and then still a quantitative yield! Its worth a publication!” Well it never came to that.

But today I suddenly remembered it.

Anyways here is the procedure of the synthesis:

In a solution of 35.3 grams (0.198 moles) 5,7-dihydroxy-2,3-dimethylbenzofurane and 60 milliliter (0.595 moles) 2-chloro-3-butanone in 1.5 liter acetone, 30.1 gram (0.281 moles) potassium carbonate is added. The whole solution / suspension is magnetically stirred under reflux for 5 days. In a oven dried installation sealed with calcium chloride tube. After these 5 days the acetone solute is evaporated and the residue is taken up in 500 ml water, extracted 3 times with 200 milliliter diethyl ether, the combined ether solutions were dried with 200 milliliter brine, and dried on magnesium sulfate for one night, after filtration and evaporation 61.5 grams (98%) brown oil as crude product was obtained, according to H-NMR almost pure 5,7-di(1-butoxy-3-on)-2,3-dimethylbenzofurane. After Kugelrohr distillation 40.8 grams (65%) dark sticky oil as pure product was obtained.


normal matter, dark matter and doesn’t matter

It seems that 20% of the matter in the universe is dark matter and that 75% is so called dark energy, and that only 5% is matter made up of atoms (protons, neutrons and electrons). The astrophysicist need the dark matter and dark energy in their models of the universe, otherwise the universe is not stable and the stars in the galaxies could not all circle around the center with the same speed.

Stars further from the center or closer to the center, doesn’t seem to make any difference, all circling with the same speed. Here comes dark matter into play.

The enormous speeds galaxies move away from each other, expanding the universe volume, here comes dark energy into play.

Scientists try to find The Holy Grail of Science: A dark matter particle and a dark energy particle. Knowing that dark matter and dark energy is completely invisible for our normal matter world.

What if the Universe is indeed a simulation? A computer simulation? Our reality is only bits and bytes? We are running on a computer inside the real, eternal and infinite Universe. Then the Software Architect of our computer simulation could have programmed dark matter and dark energy behavior in to the program, so dark matter and dark energy are only features inside the source code. OK for us invisible behavior patterns of the Universe simulation.

Some scientists are very frustrated that they build and develop the most sensitive and expensive detectors, only to have as biggest probability to find nothing 😦