1-Bromo-3-methylbutane → cis-2-methyl-7-octadecene

HRID 861708Notes

Reaction equation

HRID 861708 reaction equation
[Mg].Cl[CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:17](Br)[CH2:18][CH:19]([CH3:21])[CH3:20]>O1CCCC1>[CH3:20][CH:19]([CH2:18][CH2:17][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:21]

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 5462224MagnesiumHCID 15300631HCID 15300631, compound

Product 1

HCID 6242671cis-2-methyl-7-octadeceneYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 1-liter reactor, a Grignard reagent was prepared from 5.0 g (0.206 mole) of magnesium and 46 g (0.2 mole) of 1-chloro-cis-3-tetradecene in exactly the same manner as in Example 4. Next, 30 g of tetrahydrofuran, 30 g (0.2 mole) of isoamyl bromide and 0.6 g of cuprous iodide were placed in another 1-liter reactor and cooled to 0° C. Then, the above-described Grignard reagent was added dropwise thereto so that the temperature did not exceed 20° C. After completion of the reaction, the reaction product was distilled in exactly the same manner as in Example 4 to obtain 20 g of 2-methyl-cis-7-octadecene (purity 96.0%, yield 77%, b.p. 155°-158° C./2 mmHg). MS(m/e): 56(100%), 266 (M+, 27%).

Workup

  1. customdid not exceed 20° C
  2. customAfter completion of the reaction
  3. distillationthe reaction product was distilled in exactly the same manner as in Example 4

Sources & evidence

ORD record
ord-d0c077c0cdf045c8a3ab0992e0da27c4
Source dataset
uspto-grants-1998_02
Patent number
US05714649

Reaction notes

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