Triethoxysilane → (Z)-dodec-7-enol

Participants

Reaction Steps

To a solution of rhodium(III) chloride trihydrate (1.3 mg, 0.005 mmol), copper(II) nitrate hemipentahydrate (5.8 mg, 0.025 mmol) in THF (2.5 mL) and water (0.5 mL) was added 7-dodecyn-1-ol (91 mg, 0.50 mmol). The solution was stirred for 5 minutes and then triethoxysilane (0.21 g, 0.23 mL, 1.25 mmol) was added. The solution was stirred at room temperature for 8 hours. The volatiles were removed in vacuo and a solution of hexane (5 mL) and ether (1 mL) was added. The solution was dried over magnesium sulfate and filtered through a one inch plug of silica gel. The substrate was diluted with hexane/ether (5:1). The solvent was removed in vacuo. The product was then added to a solution of 3N hydrochloric acid (3 mL) and stirred at room temperature for 1 hour. The aqueous layer was extracted with ether (3×10 mL). The combined organics were dried over magnesium sulfate and filtered. The solvent was removed in vacuo to afford 0.088 g (0.48 mmol, 96%) of Z-7-Dodecen-1-ol which was a 14:1 Z:E mixture by spectroscopic analysis. Spectral analysis of the Z-isomer: IR (neat) 3434.8, 2929.0, 2857.1, 1459.2, 1056.1 cm-1 ; 1H NMR (300 MHz, CDCl3) δ 5.33 (m, 2 H), 3.62 (t, J=6.6 Hz, 2 H), 2.01 (br d, 4 H), 1.66 - 1.5 (m, 2H), 1.33 - 1.22 (m, 11 H), 0.88 (t, J=7 Hz, 3 H); 13C NMR (75 MHz, CDCl3) δ 129.99, 129.67, 62.96, 32.74, 32.49, 31.93, 31.21, 29.69, 29.05, 28.58, 27.10, 26.90, 25.63, 22.32, 18.41, 13.99.

Provenance & Evidence