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Reduction of 4-formyltetrathiafulvalene; 4-(hydroxymethyl)tetrathiafulvalene

SyntheticPage 293
DOI: 10.1039/SP293
Submitted Jul 25, 2008, published Jul 25, 2008
Nikola Paul Chmel (n.chmel@warwick.ac.uk)
A contribution from Scott group, Warwick University


			Reaction Scheme: Reduction of 4-formyltetrathiafulvalene

Chemicals Used

4-formyltetrathiafulvalene [[[291|Page 291]]],
sodium borohydride,

Procedure

4-formyltetrathiafulvalene (1.0 g, 4.3 mmol) was dissolved in methanol (40 ml). NaBH4 (0.18 g, 4.75 mmol) was added portion-wise and the mixture was stirred for 30 min. DCM (50 ml) was added and the mixture was washed with brine (2 × 25 ml) and water (2 × 25 ml), and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. Resulting thick brown oil was dried in vacuum oven overnight. Stored in the glove box. Yield 0.83 g (83%)

Author's Comments

Product was used in subsequent reaction without further purification. Additional purification possible by column chromatograpny. Peak 111.5 ppm on 13C NMR visible only on long exposition spectrum.

Data

1H NMR (400 MHz, CDCl3, 298 K) 2.25 (s, 1H, OH), 4.38 (s, 2H, CH2), 6.21 (s, 1H, CH), 6.30 (s, 2H, CH) 13C NMR (100 MHz, CDCl3, 298 K) 60.6 (CH2), 109.5, 111.5 (C=C), 115.4, 119.0, 119.1 (CH), 136.6 MS (ESI+) m/z: 233.8

Lead Reference

Garin, J.; Orduna, J.; Uriel, S.; Moore, A. J.; Bryce, M. R.; Wegener, S.; Yufit, D. S.; Howard, J. A. K. Synthesis 1994, 489-493.

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Keywords: tetrathiafulvalene, TTF, reduction, alcohols, aldehydes, heterocyclic compounds, sulphides

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