TBDMS protection of 2,5-hydroxybenzaldehyde; 5-OTBDMS-2-hydroxybenzaldehyde
SyntheticPage 661
DOI:
10.1039/SP661
Submitted Jul 25, 2013, published Jul 29, 2013
Chemicals Used
2,5-hydroxybenzaldehyde (Alfa Aesar)
TBDMSCl (Aldrich)
Imidazole (Aldrich)
Dichloromethane (distilled over potassium)
Procedure
To a solution of 2,5-hydroxybenzaldehyde (1.24 g, 8.97 mmol) in dry dichloromethane (20 cm3) were added TBDMSCl (1.35 g , 8.97 mmol) and imidazole. (0.61 g, 8.97 mmol) The mixture was stirred overnight and filtered to remove all insoluble material. All volatiles were removed under reduced pressure and the remaining solid (88% purity by 1H NMR) recrystallised from hot hexanes. (1.40 g, 62%)
Author's Comments
Data
1H NMR (400 MHz, CDCl3): δ no ArOH observed, 9.16 (s, 1H, HC=O), 6.85 (dd, 1H, 3J = 8Hz, 4J = 2 Hz, ArH), 6.73 (d, 1H, 4J = 2Hz, ArH), 6.68 (d, 1H, 3J = 8Hz ArH).
Lead Reference
J. M. Becker, J. Barker, G. J. Clarkson, R. van Gorkum, G. K. Johal, R. I. Walton and P. Scott,
Dalton Transactions, 2010,
39, 2309-2326.
http://dx.doi.org/10.1039/b905706d
Other References
Liu, A., Dillon, K., Campbell, R. M., Cox, D. C. and Huryn, D. M.,
Tetrahedron Lett, 1996, 37, 37850
http://dx.doi.org/10.1016/0040-4039(96)00713-7.
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Keywords: addition, aldehydes, alkenes, aromatics/arenes, protection, TBDMSCl