(4Z,7Z)-4,7-Decadien-1-yl Acetate Synthesis Without Protecting Groups
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Solution Overview
Problem
The existing method for producing (4Z,7Z)-4,7-decadien-1-yl acetate, a sex pheromone for the lesser date moth, has low yield, is costly due to the use of expensive catalysts like Amberlyst-15, and requires multiple steps with protective groups, making it inefficient for industrial production.
Innovation Solution
A process involving the reduction of 10-halo-3,6-decadiyne to form (3Z,6Z)-10-halo-3,6-decadiene, which is then converted into (4Z,7Z)-4,7-decadien-1-yl acetate without using protective groups, reducing the number of steps and increasing yield.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If the existing method using THP protecting group and Amberlyst-15 catalyst is employed, then the product can be obtained with certain purity, but the total yield is low (30%) and the production cost is high
Solution Approach 1:
The invention removes the THP protecting group entirely from the synthesis pathway. By using 10-halo-3,6-decadiyne as the starting material and performing direct reduction and substitution reactions, the method eliminates the need for protection and deprotection steps, thereby increasing overall yield while maintaining product purity through selective reaction conditions
Solution Approach 2:
The invention changes the reaction parameters by using specific reagents (LiAlH4 for reduction, NaOAc for substitution) and controlling reaction conditions (temperature, solvent system) to achieve high-yield transformations without requiring expensive catalysts like Amberlyst-15, thus improving both yield and cost-effectiveness while maintaining product quality
2Ease of manufacture
If Amberlyst-15 catalyst is used for deprotection and acetylation, then the reaction can proceed, but the cost increases and filtration becomes difficult in industrial settings
Solution Approach 1:
The invention replaces the expensive, reusable Amberlyst-15 solid acid catalyst with simple, inexpensive reagents like NaOAc that dissolve in the reaction medium. This substitution eliminates the need for complex filtration equipment and procedures, making the process more suitable for industrial production while maintaining reaction effectiveness
Solution Approach 2:
The invention replaces the mechanical filtration step required for solid catalyst removal with a solution-based chemical approach. By using soluble reagents and conducting reactions in appropriate solvents, the method eliminates the need for mechanical separation equipment, simplifying the overall manufacturing process
3Stability of the object's composition
If THP protecting group is used, then the hydroxyl group can be protected during synthesis, but the number of reaction steps increases and yield decreases
Solution Approach 1:
The invention extracts and removes the protecting group concept from the synthesis pathway. By selecting 10-halo-3,6-decadiyne as the starting material, the hydroxyl group is never introduced, eliminating the need for any protection strategy. The synthesis proceeds through direct reduction of the alkyne and substitution of the halogen, completing the transformation in fewer steps with higher cumulative yield
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This method achieves a high yield of (4Z,7Z)-4,7-decadien-1-yl acetate with fewer steps and without the need for protective groups, making it more cost-effective and suitable for industrial production.
Implementation Method 1
The resulting reaction mixture was subjected to a known reduction method using a Lindlar catalyst to give a (3Z,6Z)-10-halo-3,6-decadiene
Implementation Method 2
The resulting reaction mixture was subjected to a known reduction method using a Lindlar catalyst to give a (3Z,6Z)-10-halo-3,6-decadiene
Implementation Method 3
converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom
Data Source
AI summary
One object of the invention is to provide a high-yield process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate, with reduced number of steps, without using a protecting group. A process for preparing (4Z,7Z)-4,7-decadien-1-yl acetate is provided, the process comprising at least the following steps: reducing a 10-halo-3,6-decadiyne of the general formula (1) to form a (3Z,6Z)-10-halo-3,6-decadiene of the general formula (2); and converting the (3Z,6Z)-10-halo-3,6-decadiene into (4Z,7Z)-4,7-decadien-1-yl acetate of the formula (4) having an acetoxy group in place of the halogen atom of the (3Z,6Z)-10-halo-3,6-decadiene.