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Reduction of 3,4-dihydro-5H-benzo[cd]pyren-5-one.; 3,4-dihydro-5H-Benzo[cd]pyren-5-ol

SyntheticPage 536
DOI: 10.1039/SP536
Submitted Feb 09, 2012, published Mar 12, 2012
Anish Mistry (a.mistry@warwick.ac.uk)
A contribution from Fox Group, Warwick University


			Reaction Scheme: <IMG src="/images/empty.gif">Reduction of <SPAN id=csm1338455030727 class="csm-chemical-name csm-not-validated" title=3,4-dihydro-5H-benzo[cd]pyren-5-one grpid="1">3,4-dihydro-5H-benzo[cd]pyren-5-one</SPAN>.<IMG src="/images/empty.gif">

Chemicals Used

3,4-dihydro-5H-Benzo[cd]pyren-5-one (prepared)
LiAlH4 (1 equiv, Alfa Aesar)
THF
Diethyl ether

Procedure

Under a dinitrogen atmosphere, lithium aluminium hydride (3 mg, 0.08 mmol) in diethyl ether was stirred at 0oC. The 3,4-dihydro-5H-Benzo[cd]pyren-5-one (20 mg, 0.08 mmol) was dissolved in THF and added to the mixture slowly and the solution left to stir at room temperature for 1 h.

After 1 hour, water and then HCl was added (1:3) sequentially under a dinitrogen atmosphere.
The organics collected and dried with Na2SO4 and solvent removed under vacuo, to obtain a crude orange solid.

The crude was columned using (8:2) petroleum ether: ethyl acetate to obtain a pinkish powdered solid (19 mg, 94%).

Author's Comments

Particular care should be taken when quenching the reaction due to any unreacted Lithium Aluminium Hydride.

Data

δH(500MHz, CDCl3) ppm: 2.30 - 2.43 (2H, m, HO-CH2-CH2), 3.37 (1H, ddd, J 5.0, 7.0, 16.5, HO-CH2-CH2), 3.58 (1H, ddd, J 5.0, 8.0, 16.5, HO-CH2-CH2), 5.29 (1H, dd, J 3.5, 7.0, HO-CH), 7.83 (1H, d, J 8.0, aryl), 7.96 - 8.17 (7H, m, aryl).           

Lead Reference

Selective Reductions. XII. Explorations in Some Representative Applications of Aluminum Hydride for Selective Reductions,
Nung Min Yoon, Herbert C. Brown, JACS., 90.11, 1968.

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Get structure file (.cdx, .sk2, .mol)

Keywords: ketones, reduction

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