(E)-3,7-Dimethylocta-2,6-diene-1-thiol synthesis
- Product Name:(E)-3,7-Dimethylocta-2,6-diene-1-thiol
- CAS Number:39067-80-6
- Molecular formula:C10H18S
- Molecular Weight:170.31
![Thioacetic acid S-[(E)-3,7-dimethyl-2,6-octadienyl] ester](/CAS/GIF/71173-67-6.gif)
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Yield: 61%
Reaction Conditions:
with lithium aluminium tetrahydride in tetrahydrofuran at 0; for 4 h;
Steps:
(E)-3,7-Dimethylocta-2,6-diene-1-thiol (50)
A solution of 48 (846 mg, 3.98 mmol) in anhydroustetrahydrofuran (10 mL) cooled at 0 °C was treated with portionwise with lithium aluminum hydride(181 mg, 4.74 mmol). The mixture was stirred at 0 °C for 4 h. The reaction was quenched by addition ofethyl acetate (2.0 mL). Then, the mixture was partitioned between methylene chloride (50 mL) and anaqueous saturated solution of potassium tartrate (50 mL). The organic phase was washed with water(2 30 mL), dried (MgSO4), and the solvent was evaporated. The product was purified by columnchromatography (silica gel) eluting with hexane to give 411 mg (61% yield) of 50 as a colorless oil:1H NMR (500.13 MHz, CDCl3) δ 1.40 (t, J = 7.1 Hz, 1H, SH), 1.60 (s, 3H, H-8), 1.66 (d, J = 1.2 Hz, CH3 atC-7), 1.68 (d, J = 1.2 Hz, CH3 at C-3), 2.00 (m, 2H, H-4), 2.07 (m, 2H, H-4), 3.16 (ddd, J = 7.6, 7.3, 0.4 Hz, 2H, H-1), 5.08 (tq, J = 6.9, 1.4 Hz, 1H, H-6), 5.34 (tsxt, J = 7.8, 1.3 Hz, 1H, H-2); 13C NMR (125.77 MHz,CDCl3) δ 15.8 (CH3 at C-2), 17.7 (CH3 at C-6), 22.1 (C-1), 25.7 (C-8), 26.4 (C-5), 39.4 (C-4), 123.3 (C-2),123.6 (C-5), 131.7 (C-7), 137.5 (C-3). HRMS (ESI) calcd. for C10H19S [M + H]+ 171.1207; found 171.1194.
References:
Galaka, Tamila;Casal, Mariana Ferrer;Storey, Melissa;Li, Catherine;Chao, María N.;Szajnman, Sergio H.;Docampo, Roberto;Moreno, Silvia N.J.;Rodriguez, Juan B. [Molecules,2017,vol. 22,# 1,art. no. 82]
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