1,2-Dibromoethane → 5,9,13-Pentadecatrien-2-one, 6,10,14-trimethyl-

HRID 1461132Notes

Reaction equation

HRID 1461132 reaction equation
[Mg].[CH2:2](Br)CBr.[CH2:6](Cl)/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9].ClC[C:19](=[CH:23][CH2:24][CH2:25][CH3:26])[C:20](=[O:22])[CH3:21]>[Cl-].[Zn+2].[Cl-].[Cu]I.O1CCCC1>[CH2:23]([CH2:19][C:20](=[O:22])[CH3:21])[CH:24]=[C:25]([CH2:26][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:2]

Participants

8

Reactant 4

HCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 6372219Geranyl chlorideHCID 729650523-Chloromethylheptenone

Product 1

HCID 612065,9,13-Pentadecatrien-2-one, 6,10,14-trimethyl-Yield 78.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The same procedure as that described in Example 25 was repeated except that 0.73 g of metallic magnesium, 80 ml of tetrahydrofuran, three droplets of ethylene dibromide, 7.4 g (0.03 mol) of geranyl chloride having a purity of 70%, 4.1 g (0.03 mol) of anhydrous zinc chloride, 0.2 g of CuI, 3 g (0.02 mol) of 3-chloromethylheptenone and 30 ml of tetrahydrofuran were used. Thus, 4.1 g of the objective compound was obtained as a colorless liquid (yield: 78.2%, purity: 98.8%).

Sources & evidence

ORD record
ord-2396031ef8544ca5a04cfd9f812d86a2
Source dataset
uspto-grants-1991_12
Patent number
US05073659

Reaction notes

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