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

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%)

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.

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

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.