3-Chlorocyclopent-1-ene → HCID 13924082, compound

HRID 1789558Notes

Reaction equation

HRID 1789558 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([O:9][CH2:10][CH3:11])[CH2:7][CH3:8].[Mg].Cl[CH:14]1[CH2:18][CH2:17][CH:16]=[CH:15]1>O1CCCC1>[CH2:10]([O:9][CH:6]([CH2:7][CH3:8])[CH2:5][CH2:4][CH2:3][CH2:2][CH:18]1[CH2:17][CH2:16][CH:15]=[CH:14]1)[CH3:11]

Participants

5

Reactant 3

HCID 72973-Chlorocyclopent-1-eneHCID 5462224MagnesiumHCID 139240811-Chloro-5-ethoxyheptane2×

Product 1

HCID 13924082HCID 13924082, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

The procedure followed is the same as that described in Example 8 with the following substitutions made: the starting material prepared in Example 38, 1-chloro-5-ethoxyheptane (162 g, 1.13 moles) dissolved in tetrahydrofuran (162 ml), granular magnesium (50 g, 2.1 moles) in tetrahydrofuran (500 ml), Li2CuCl4 (29.1 mmoles), and 3-chlorocyclopentene (89 g, 0.86 moles) diluted in 100 ml tetrahydrofuran was used. The crude product is distilled under reduced pressure leaving a clear, colorless oil (121 g, 0.575 moles), BP 76° C./0.34 mm.

Workup

  1. distillationThe crude product is distilled under reduced pressure

Sources & evidence

ORD record
ord-a625257d3ef147089e923ee98322cb61
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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