Submit a SyntheticPage About SyntheticPages Page Index Browse most recent SyntheticPages View the Leaderboard We value your feedback
SyntheticPages
  Navigation Buttons


Back to List

Log In

Join Now

Print Version

Home

About this site

Privacy Policy







Copyright Syntheticpages ©2001




Mitsonobu condensation of N-hydroxyphthalimide and an alkanol.; N-Alkoxyphthalimides.

SyntheticPage 143 (2001)
Submitted 28th Aug 2001, published 28th Aug 2001

Andrew McCarroll ([email protected]),
A contribution from the Walton Group, St Andrews



Chemicals Used
THF (dry) i-propanol N-hydroxyphthalimide DEAD (Aldrich) Triphenylphosphine Ether Sodium carbonate

Procedure
To THF (100 cm3) at 0 oC was added i-propanol (0.56 g; 9.25 mmol), N-hydroxyphthalimide (3.00 g; 18.5 mmol), triphenylphosphine (4.82 g; 18.5 mmol), and diethyl azodicarboxylate (3.2 cm3; 20.2 mmol) in that order. The mixture was warmed to 50 oC, and stirred at this temp for 3 days. The mixture was cooled and concentrated. Ether was added, and the solution was washed 5 times with saturated sodium carbonate solution. The aqueous layers were back extracted with ether, and the organic layers dried (MgSO4) and concentrated. The product was purified by column chromatography (PE/ether) to give colourless crystals (1.61 g; 85%)

Author's Comments
The extraction is messy, due to sodium carbonate constantly crashing out of solution. The yield does not appear to be affected. When performing the column, it is better if the petrol and ether are premixed in the silica, to prevent bubbling on the column when ether meets silica for the first time. The notorious triphenylphosphine oxide was not found to be a problem. The reaction also worked with dodecanol (69% yield) (and should work with most simple primary and secondary alcohols), but not with t-butanol, for which a different procedure needs to be used (A. Chimiak and T. Kolasa, Rocz. Chim., 1974, 48, 139.) The reaction was not performed on any scale other than that described.

Data
m.p. 52-54 oC. 1H nmr (300MHz, CDCl3) 1.38 (6H, t, J=6.0 Hz), 4.51-4.59 (1H, septet, J=6.3Hz), 7.73-7.87 (4H,m)


Lead Reference
A. J. McCarroll and J. C. Walton, J. Chem Soc. Perkin Trans. 1, 2000, 1868-1875.

Other References
P. T. Gallagher, J. C. A. Hunt, A. P. Lightfoot and C. J. Moody, J. Chem. Soc. Perkin Trans. 2, 1997, 27, 2633. E. Grochowski and J. Jurczak, Synthesis, 1976, 682. A. Chimiak and T. Kolasa, Bull. Acad. Pol. Sci. Ser. Chim., 1974, 22, 195.

This page has been viewed approximately 162 times since records began.

Get CDX file (Choose "Open this file from its current location" TWICE)

SyntheticPagesTM are for use exclusively by those with training and experience in synthetic chemistry. While contributors are asked to identify hazards and to use methods designed to reduce risk, no formal hazard or risk assessments are included, and these procedures must be conducted at one's own risk. SyntheticPages, its editors, owners and associates do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. Copyright ©2004 Synthetic Pages

Comment on this page!

Registered users may add comments to other pages. If you have already registered, please log in, otherwise you may register here.

Back to List

Back to Top

By using this site, you agree to its Terms and Conditions