Diisopropylamine,
2.5 M solution of nBuLi in hexane,
tetrathiafulvalene (TTF) Page 290],
2M HCl,
THF (distilled over potassium, degassed),
diethyl ether (distilled over sodium/potassium alloy, degassed),

A solution of LDA was prepared in situ. Diisopropylamine (1.54 ml, 0.011 mol) was dissolved in dry THF (5 ml) under argon, and cooled to -78°C. 2.5 M solution of nBuLi in hexane (4.4 ml, 0.011 mol) was added dropwise. The mixture was allowed to warm up to ambient temperature and was stirred for 2 hours. TTF (2.0 g, 0.01 mol) was dissolved in dry Et₂O (120 ml) under argon and cooled to -78°C. The solution of LDA was added dropwise over a period of 5 min. and the mixture was stirred for 1.5 hours at -78°C. N-methyl-N-phenylformamide (2.4 ml, 0.02 mol) was added dropwise, stirring was continued for another 3 hours. The dry ice/acetone bath was replaced with dry ice/CH₃CN (-40°C) and the mixture was allowed to warm up slowly overnight to ambient temperature. The mixture was diluted with water (60 ml) and acidified with 2M HCl (20 ml). The product was extracted with DCM (3×40 ml) and the collected DCM fractions dried over MgSO₄. The product was purified by flash chromatography, unreacted TTF was washed off initially with toluene:hexane (1:1). Elution with DCM yielded product as deep red solid. Traces of N-methyl-N-phenylformamide were washed off with Et₂O. Yield 1.62 g (70%).

Used in subsequent reaction. Stored in vacuum dessicator.

Anal calcd. for C₆H₄S₄: C 36.19%, H 1.74%, S 55.20%. Found: C 36.42%, H 1.81%, S 55.14%. ¹H NMR (400 MHz, CDCl₃, 298 K) 6.34 (2×d, 2×1H, ³J_HH=6Hz, ³J_HH=6Hz, CH), 7.42 (s, 1H, CH), 9.47 (s, 1H, CHO) ¹³C NMR (100 MHz, CDCl₃, 298 K) 105.49, 115.95, 118.69, 119.36, 139.82, 141.54, 179.63 MS (ESI+) m/z: 231.91

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

Coles, S. R., University of Warwick, 2006