Supply missing Reagent A (Synthesis)

asked by @christopherd31 • 12 months ago • Organic Chemistry • 5 pts

Supply missing reagent A and product B in the following synthetic scheme. No stereochemistry needed. Product B is propranolol, an antihypertensive agent used in the treatment of high B.P.

  • Hey there! I think you forgot to attach the image. Can you kindly follow it up? Thanks! Reyn commented 12 months ago
  • Sorry, I accidentally posted the image in the answer section. Christopher commented 12 months ago
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answered by @christopherd31 • 12 months ago

Seems like the first reaction is a Williamson ether reaction where we will use NaH to deprotonate that -OH group. Then we can now add an alkyl halide that fits the given product. I drew A below.

For B, this is a base-catalyzed epoxide ring opening that favor addition to the LEAST substituted carbon (kinetic control). So the amine gets attached to the least substituted C while -OH will be present at the secondary carbon. I also drew both enantiomers of B. enter image description here

You can also watch the related reactions here:

Williamson Ether Synthesis:https://www.clutchprep.com/organic-chemistry/ether-synthesis/?c_id=453

Base-Cat Epoxide opening:https://www.clutchprep.com/organic-chemistry/epoxide-ring-opening-2/?c_id=453

Hope that helps

answered by @reyn • 12 months ago