Sodium hydride → Ethyl 6,12-dithiatetradecanoate

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Reaction Steps

NaH (0.4 g, 8.4 mmol) was washed with hexanes and then suspended in dry THF (55 mL). 5-Ethylthiopentanethiol (8 mmol, 73% pure by GC analysis, contaminated by 1,5-bis(ethylthio)pentane, 1.80 g of mixture) in THF (8 mL) was added and stirred for 1 h at room temperature. Ethyl 5-iodovalerate (2.1 g, 8 mmol) in THF (8 mL) was added and the mixture refluxed for 8 h. The solvent was evaporated in vacuo, the residue was dissolved in EtOAc (150 mL), washed with water (2 ×50 mL), brine (50 mL), dried (Na2SO4), chromatographed (silica gel, EtOAc/hexanes 1:10) and distilled (Kugelrohr) to yield the title compound (1.86 g, 80%) as a colorless oil (bp 147° C.-149° C./0.2 torr). IR (neat): 1740 cm-1. 1H-NMR: 1.25 (t, 6H); 1.50 (quintet, 2H); 1.54- 1.67 (m, 6H); 1.73 quintet, 2H); 2.32 (t, 2H); 2.46-2.57 (m, 8H); and 4.12 (q, 2H). Anal. Calcd for C14H28S2O2 : C, 57.49; H, 9.65%. Found: C, 57.36; H, 9.59%.

Provenance & Evidence