Реакция #56704

Уравнение реакции

ammonium chloride

methylmagnesium chloride

(S)-citronellyl bromide

LiCl

→

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

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   ТемператураAfter 10 hours the solution was cooled to 0° C.
2. 2
   ДругоеThe resultant two layers were separated
3. 3
   Экстракцияthe aqueous phase extracted with ether
4. 4
   СушкаThe combined organic phases were dried (MgSO4)
5. 5
   Концентрированиеconcentrated

Методика

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.

Источник