Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. CI OMe OMe OMe 'N' HN N CI. + НО, Chloroacetic acid (S)-Metolachlor 3 NH2 CI + MEOH OMe Acetone Methanol 2-Ethyl-6-methylaniline Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.

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Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor
from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol.
CI
OMe
OMe
OMe
'N'
HN
N
CI.
+ НО,
Chloroacetic acid
(S)-Metolachlor
3
NH2
CI
+ MEOH
OMe
Acetone
Methanol
2-Ethyl-6-methylaniline
Show reagents and experimental conditions for the synthesis of Metolachlor from these
four organic starting materials. Your synthesis will most likely give a racemic mixture.
The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric
excess of the S enantiomer.
Transcribed Image Text:Following is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. CI OMe OMe OMe 'N' HN N CI. + НО, Chloroacetic acid (S)-Metolachlor 3 NH2 CI + MEOH OMe Acetone Methanol 2-Ethyl-6-methylaniline Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.
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