3-Chlorocyclopent-1-ene → 3-(3-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene

HRID 1789552Notes

Reaction equation

HRID 1789552 reaction equation
Cl[CH2:2][CH2:3][CH:4]([CH2:13][CH3:14])[O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].Cl[CH2:16][CH2:17][CH:18](O[Si](CC(C)C)(C)C)[CH2:19][CH3:20].[Mg].ClC1CCC=C1>O1CCCC1>[CH3:10][C:9]([Si:6]([CH3:8])([CH3:7])[O:5][CH:4]([CH2:13][CH3:14])[CH2:3][CH2:2][CH:19]1[CH2:18][CH2:17][CH:16]=[CH:20]1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 72973-Chlorocyclopent-1-eneHCID 5462224MagnesiumHCID 86741753(5-Chloro-3-pentyloxy)(2,2-dimethylethyl)dimethylsilane {3-chloro-1-ethylpropoxy)(1,1-dimethylethyl) dimethylsilane

Product 1

HCID 139240763-(3-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

The procedure followed is the same as that described in Example 8 substituting (5-chloro-3-pentyloxy)(2,2-dimethylethyl)dimethylsilane {3-chloro-1-ethylpropoxy)(1,1-dimethylethyl)dimethylsilane} (78 g, 0.33 moles) diluted in tetrahydrofuran (100 ml), granular magnesium (24 g, 1.00 moles), tetrahydrofuran (100 ml), 0.1M solution of Li2CuCl4 (1.0 mmole), and 3-chlorocyclopentene (33 g, 0.33 moles) dissolved in tetrahydrofuran (50 ml). The crude product is distilled under reduced pressure leaving a clear yellow oil (21 g, 0.078 moles), BP 69° C./0.1 mm.

Workup

  1. distillationThe crude product is distilled under reduced pressure

Sources & evidence

ORD record
ord-3ba57ccfe5a34447a527ebdf41b92a16
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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