Реакция #1018

Уравнение реакции

sodium ethoxide

4-pyridine carboxaldehyde

(3-cyclopentyloxy-4-methoxyphenyl)-methyltriphenylphosphonium chloride

→

compound

Выход 11.9%

(Z)-4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)ethenyl]pyridine

Выход 11.9%

Растворители

ethanol

ethanol

Условия реакции

Обработка

1. 1
   КонцентрированиеAfter 2h, the reaction mixture was concentrated in vacuo
2. 2
   Другоеthe residue partitioned between EtOAc (75 ml) and brine (50 ml)
3. 3
   ДругоеThe organic layer was separated
4. 4
   Сушкаdried (MgSO4)
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   workup.ADDITIONconsisted of a 3:2 mixture of (Z)

Методика

A solution of sodium ethoxide [prepared from sodium (0.10 g, 4.50 mmol)] in ethanol (50 ml) was added over 5 min to a stirred mixture of 4-pyridine carboxaldehyde (0.44 g, 4.10 mmol) and (3-cyclopentyloxy-4-methoxyphenyl)-methyltriphenylphosphonium chloride (2.00 g, 4.08 g) in ethanol (30 ml). After 2h, the reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc (75 ml) and brine (50 ml). The organic layer was separated, then dried (MgSO4) and concentrated in vacuo. A 1H n.m.r. spectrum indicated that the mixture consisted of a 3:2 mixture of (Z): (E)title compound (and triphenylphosphine oxide). A portion (0.6 g) of the mixture was subjected to chromatography (SiO2 ; hexane to EtOAc) to afford pure/Z-title compound (0.14 g) as a pale yellow solid m.p. (Found: C, 77.18; H, 7.16; N, 4.63. C19H21NO2 requires C, 77.26; H, 7.17; N, 4.74%); δH (300 MHz; CDCl3) 1.5-1.55 (2H, br m, cyclopentyl H's), 1.65-1.9 (6H, br m, cyclopentyl H's), 3.83 (3H, s, OMe), 4.44 (1H, br m, OCHCH2), 6.40 (1H, d, J 12.2 Hz, CH=CH), 6.65-6.80 (4H, m, ArH ortho to OMe+2×ArH meta to OMe+CH=CH), 7.15 (2H, ca. d, J 6.0 Hz, pyridine H2, H6); m/z 295 (M+, 22%), 228 (15), 227 (100), 226 (94), 198 (35), 184 (15), 166 (12), 43 (19), and 41 (29).

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