Reaktion #2039

Reaktionsgleichung

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

triphenylphosphine

bromine

→

product 17

Ausbeute 90.0%

Z-1-Bromodec-4-ene

Ausbeute 90.0%

Lösungsmittel

methylene chloride

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle