Sodium hydride → Ethyl 6,12-dithiatetradecanoate

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°-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%.

1. temperaturethe mixture refluxed for 8 h
2. customThe solvent was evaporated in vacuo
3. dissolutionthe residue was dissolved in EtOAc (150 mL )
4. washwashed with water (2×50 mL), brine (50 mL)
5. dry with materialdried (Na2SO4)
6. customchromatographed (silica gel, EtOAc/hexanes 1:10)
7. distillationdistilled (Kugelrohr)

ORD record

ord-d2e9ebf1fc934df297d1146a9e8d85e2

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05571689