How do I make imgur dot com/kvxVZEv from cyclohexanone. Stork enamine synthesis results in a primary alcohol but I need secondary alcohol with one more carbon atom at right end.
To make the desired compound (imgur dot com/kvxVZEv) from cyclohexanone, you can use a reaction sequence known as the Stork enamine synthesis followed by a modification step to introduce an additional carbon atom at the right end to obtain a secondary alcohol.
Here is a step-by-step explanation of how to achieve this:
Step 1: Stork Enamine Synthesis
Start with cyclohexanone, which is a ketone. To convert it into an enamine, follow these steps:
1. React cyclohexanone with ethyl vinyl ether (or another suitable nucleophile) in the presence of a catalytic amount of a mild Lewis acid, such as p-Toluenesulfonic acid (p-TsOH).
2. The Lewis acid will activate the carbonyl group of cyclohexanone, allowing it to undergo nucleophilic addition with the ethyl vinyl ether, resulting in the formation of the enamine.
3. The product of this step should be an enamine of cyclohexanone. This intermediate consists of a double bond between the α-carbon (carbon adjacent to the carbonyl carbon) and the nitrogen atom.
Step 2: Introduction of a Carbon Atom
To introduce an additional carbon atom at the right end of the molecule, we can perform the following steps:
1. Treat the enamine intermediate obtained from Step 1 (cyclohexanone enamine) with an aldehyde (e.g., formaldehyde) in the presence of an acid catalyst, like acetic acid or hydrochloric acid.
2. The acid catalyst promotes an aldol condensation reaction, leading to the formation of a β-hydroxyketone (secondary alcohol with one more carbon atom at the right end). This is achieved by the nucleophilic addition of the enamine to the aldehyde, followed by a dehydration step.
The resulting compound should closely resemble the structure you mentioned (imgur dot com/kvxVZEv) – a secondary alcohol with an additional carbon atom at the right end.
Keep in mind that chemical synthesis reactions can be complex, and experimental conditions may need optimization based on the specific reactants and desired product. It is always recommended to consult relevant literature or consult with an experienced chemist to ensure accurate and efficient execution of the synthesis.