Reaktion #56704

Reaktionsgleichung

ammonium chloride

methylmagnesium chloride

(S)-citronellyl bromide

LiCl

→

(R)-2,6-dimethyl-non-2-ene

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter 10 hours the solution was cooled to 0° C.
2. 2
   SonstigeThe resultant two layers were separated
3. 3
   Extraktionthe aqueous phase extracted with ether
4. 4
   TrocknenThe combined organic phases were dried (MgSO4)
5. 5
   Einengenconcentrated

Vorschrift

To (S)-citronellyl bromide (50 g, 0.228 mol) in THF (800 mL) at 0° C. was added LiCl (4.3 g) followed by CuCl2 (6.8 g). After 30 minutes methylmagnesium chloride (152 mL of a 3 M solution in THF, Aldrich) was added and the solution warmed to room temperature. After 10 hours the solution was cooled to 0° C. and a saturated aqueous solution of ammonium chloride carefully added. The resultant two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4) and concentrated to give (R)-2,6-dimethyl-non-2-ene. 32.6 g; 93%. Used without further purification. 1H NMR(400 MHz; CDCl3) δ 5.1 (m, 1H), 1.95 (m, 2H), 1.62 (s, 3H), 1.6 (s, 3H), 1.3 (m, 4H), 1.2 (m, 2H), 0.8 (s, 6H);13C NMR (100 MHz; CDCl3) 131.13, 125.28, 39.50, 37.35, 32.35, 25.92, 25.77, 20.31, 19.74, 17.81, 14.60.

Quelle