Réaction #2039

Équation de réaction

(4Z)-1-(tetrahydropyran-2-yloxy)-4-decene

triphenylphosphine

bromine

→

product 17

Rendement 90.0%

Z-1-Bromodec-4-ene

Rendement 90.0%

Solvants

methylene chloride

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   AutreIsolation and purification by conventional means

Mode opératoire

To an ice-cool solution of triphenylphosphine (0.72 g, 2.74 mmol) and bromine (0.41 g, 2.6 mmol) in CH2Cl2, a solution of (4Z)-1-(tetrahydropyran-2-yloxy)-4-decene (16) (0.41 g, 1.71 mmol), prepared according to Example 16, in methylene chloride was added dropwise. Isolation and purification by conventional means afforded the product 17 in 90% yield (0.33 g). 1H NMR (200 MHz ) δ: 5.42 (dtt, J=11.0, 7.0, 7.0, 1.0, 1.0 Hz, 2H, CH=CH-4, 5); 3.41 (t, J=6.6, 6.6 Hz, 2H CH2 -1, 2.20 (dt, J=7.0, 7.0 Hz, 2H, CH2 -3); 2.04 (dr, J=6.5, 6.5 Hz, 2H, CH2 -6); 1.91 (tt, J=6.5, 6.5, 6.5 Hz, 2H, CH2 -2); 1.30 (m, 6H, CH2 -7, 8, 9); 0.89 (t, J=7.0 Hz, CH3). MS [EI, m/z(%)] 220 (M+ -8), 218 (M+, 8), 164 (12), 162 (12), 150 (23), 148 (23), 135 (8), 109 (12), 97 (44), 95 (14), 83 (55), 82 (14), 81 (37), 79 (15), 70 (21), 69 (100), 67 (39), 56 (29), 55 (93), 54 (20), 43 (21), 42 (20), 41 (92), 39 (30). IR (CCl4, cm-1) 3008 (cis CH=CH), 1246 (RCH2CH2Br), 649, 566 (C--Br).

Source