3-Chlorocyclopent-1-ene → 3-Heptylcyclopentene

HRID 1722377Notes

Reaction equation

HRID 1722377 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Mg].Cl[CH:11]1[CH2:15][CH2:14][CH:13]=[CH:12]1>O1CCCC1>[CH2:2]([CH:15]1[CH2:14][CH2:13][CH:12]=[CH:11]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 72973-Chlorocyclopent-1-eneHCID 123691-BromoheptaneHCID 5462224Magnesium

Product 1

HCID 139240793-HeptylcyclopenteneYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

The procedure followed is the same as that described in Exmple 8 substituting the starting material, 1-bromoheptane (100 g, 0.56 moles) dissolved in tetrahydrofuran (100 ml), granular magnesium (25 g) in tetrahydrofuran (100 ml), 0.1M solution of Li2CuCl4 (1.7 mmoles), and 3-chlorocyclopentene (57 g, 0.56 moles) dissolved in tetrahydrofuran (200 ml). The crude product is fractionally distilled under vacuum leaving a clear, colorless oil (48 g, 0.29 moles), BP 41° C./0.35 mm.

Workup

  1. distillationThe crude product is fractionally distilled under vacuum

Sources & evidence

ORD record
ord-055d6976ec394f149deecbe4db83c19e
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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