Reacción #2035

Ecuación de reacción

6

(8Z,11Z)-1-(tetrahydropyran-2-yloxy)-8,11-tetradecadien-3-yne

→

(8Z,11Z)-8,11-tetradecadien-3-yn-1-ol

Rendimiento 83.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resin was removed by filtration
2. 2
   Lavadowashed with methanol (3×20 mL)
3. 3
   OtroThe alcohol 7 was purified by flash chromatography (1.3 g, 83% yield)

Procedimiento

A solution of 6 (2.2 g, 7.5 mmol) in methanol (50 mL) was stirred with DOWEX™ 50W-X8 (Dow Chemical, Midland, Mich.) ion exchange resin (2 g) and the formation of 7 was monitored by TLC. The resin was removed by filtration and washed with methanol (3×20 mL). The alcohol 7 was purified by flash chromatography (1.3 g, 83% yield). 13H NMR (200 MHz) δ: 5.36 (m, 4H, CH=CH), 3.66 (t, J=6.1, 6.4 Hz, 2H, CH2 -1), 2.78 (t, J=6.4, 6.7 Hz, 2H, =CH--CH2 --CH=), 2.42 (tt, J=2.1, 2.4, 6.1, 6.4 Hz, 2H, CH2 -2), 2.16 (tt, J-2.1, 2.4, 7.0, 7.3 Hz, 2H, CH2 -5), 2.15 (m, 2H, CH2 -7), 2.06 (dq, J=7.3, 7.0, 7.3, 7.6 Hz, 2H, CH2 -13), 1.55 (tt, J=7.1, 7.3, 7.3, 7.3 Hz, 2H, CH2 -6), 0.96 (t, J=7.3, 7.6 Hz, 3H, CH3 -14). 13C NMR (100.6 MHz) δ: 131.9(12), 129.0(11), 128.8(9), 127.2(8), 82.3(3), 76.6(4), 61.3(1), 28.8(7), 26.2(6), 25.5(10), 23.1(5), 20.5(2), 18.2(13), 14.2(14). MS [EI, m/z(%)] 161(15), 159(20), 145(30), 133(25), 131(27), 119(34), 117(42), 105(42), 95(17), 93(27), 91(83), 79(76), 77(37), 69(22), 67(78), 65(29), 55(46), 53(39), 44(29), 43(24), 42(34), 41(100), 40(61).

Fuente