Ammonium Chloride → (6R)-2,6-Dimethylnon-2-ene

HRID 28426

Reaction equation

HRID 28426 reaction equation
[CH2:1](Br)[CH2:2][C@H:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:4].[Li+].[Cl-].[CH3:14][Mg]Cl.[Cl-].[NH4+]>C1COCC1>[CH3:9][C:8](=[CH:7][CH2:6][CH2:5][C@H:3]([CH3:4])[CH2:2][CH2:1][CH3:14])[CH3:10]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 10900106(S)-(+)-Citronellyl bromideHCID 178418332HCID 178418332, compound

Product 1

HCID 15345839(6R)-2,6-Dimethylnon-2-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. temperatureAfter 10 hours the solution was cooled to 0° C.
  2. customThe resultant two layers were separated
  3. extractionthe aqueous phase extracted with ether
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ddc9d6f6ae4348f4999a22f5dc4af579
Source dataset
uspto-grants-2008_09
Patent number
US07419981B2

Linked notes

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