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Mitsunobu coupling of an imide with an alcohol; 3,4-dimethyl-1-pent-4-enyl-pyrrole-2,5-dione

SyntheticPage 4
DOI: 10.1039/SP4
Submitted Jun 07, 2001, published Jun 08, 2001
Graham Sibley (gem.sibley@bris.ac.uk)


			Reaction Scheme: Mitsunobu coupling of an <SPAN class=csm-chemical-group id=csm1276201837635 title=imide>imide</SPAN> with an <SPAN class=csm-chemical-group id=csm1276201820895 title=alcohol>alcohol</SPAN>

Chemicals Used

2,3-dimethyl maleimide (1eq)
4-penten-1-ol (1.1eq)
diethylazodicarboxylate (1.5eq)
triphenylphosphine (1.5eq)
THF (0.2M)

Procedure

To a stirring solution of the maleimide and triphenylphosphine in THF at zero under nitrogen was added the alcohol in THF (10ml) and then DEAD dropwise. The reaction was allowed to warm to room temperature and then left stirring for 2.5 hrs after which time the reaction mixture was concentrated in vacuo. The resultant crude prduct was purified by flash column chromatography.

Author's Comments

This is a good method for forming carbon nitrogen bonds. On a large scale to remove the triphenylphosphine oxide produced the crude mixture is cooled down to zero and ether added, followed by trituration. This results in a white solid which can be removed by filteration (wash with cold ether). The mother liquor is concentrated in vacuo and purified as above.

Data

5.68-5.72 (1H, m, CH), 5.06-4.94 (2H, m, CH2), 3.49 (2H, t, CH2 J = 7.3), 1.96 (6H, s, 2 x CH3), 2.20-1.94 (2H, m, CH2), 1.69 (2H, q, CH2, J = 7.3)

Lead Reference

Kevin I. Booker-Milburn, Christopher E. Anson, Cole Clissold, Nicola J. Costin, Richard F. Dainty, Martin Murray, Dhiren Patel, Andrew Sharpe, European Journal of Organic Chemistry, 2001, 1473-1482.

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Keywords: alcohols

Post new comment
  • Guest Marcus KnappertNov 5 2015 5:44PMReview

    Thanks for the reaction. There is also a review on the topic, giving you several similar reactions in 5.1. N-Alkylation Using Phthalimide and Related Imides. See: Mitsunobu and Related Reactions: Advances and Applications, Chem. Rev. 2009, 109, 2551–2651, DOI: 10.1021/cr800278z.

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