Potassium sodium tartarate → 2-Tridecen-1-ol, (2E)-

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-tridecyn-1-ol (2 g, 10 mmol) in Et2O (50 mL) was added LiAlH4 (1 g, 26 mmol, 2.6 equiv). The resulting mixture was refluxed for 12 hours and allowed to cool to 25° C. A saturated solution of sodium-potassium tartrate was then added and the resulting mixture was stirred for an additional 3 hours. The organic layer was separated, dried (MgSO2) and concentrated by rotary evaporation to yield trans-2-tridecen-1-ol (50) as a colorless oil: 1H NMR (CDCl3) δ 5.62 (dt, J1 =15.3 Hz, J2 =5.1 Hz, 1 H), 5.70 (dt, J1 =15.3 Hz, J2 =5.7 Hz, 1 H), 4.08 (t, J=4.2 Hz, 2 H), 2.04 (q, J=6 Hz, 2 H), 1 30 (m, 16 H), 0.88 (t, J=6.9 Hz, 3 H); 13C NMR (CDCl3) δ 133.72, 128.92, 63.96, 32.31, 32.01, 29.72, 29.60, 29.43, 29.28, 29.24, 22.78, 14.20. ##STR24##

Provenance & Evidence