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

HRID 569227

Reaction equation

HRID 569227 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].[Mg].Cl[CH:17]1[CH2:21][CH2:20][CH:19]=[CH:18]1>O1CCCC1>[CH:21]1([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])[CH2:20][CH2:19][CH:18]=[CH:17]1

Participants

5

Reactant 3

HCID 72973-Chlorocyclopent-1-eneHCID 5462224MagnesiumHCID 13924075(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

Further following the procedure described in Example 6B, substituting 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), one obtains [3-(2-cyclopenten-1-yl)-1-ethylpropoxy](1,1-dimethylethyl)dimethylsilane. The crude product is distilled under reduced pressure leaving a clear yellow oil (21 g, 0.078 moles), BP 69° C./0.1 mm.

Sources & evidence

ORD record
ord-9ebf709ff1724509b056156187beed1b
Source dataset
uspto-grants-1988_03
Patent number
US04731458

Linked notes

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