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

HRID 1722375Notes

Reaction equation

HRID 1722375 reaction equation
Cl[CH2:2][CH2:3][CH:4](O[Si](CC(C)C)(C)C)[CH2:5][CH3:6].Cl[CH2:16][CH2:17][CH:18]([CH2:27][CH3:28])[O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].[Mg].ClC1CCC=C1>O1CCCC1>[CH3:24][C:23]([Si:20]([CH3:22])([CH3:21])[O:19][CH:18]([CH2:27][CH3:28])[CH2:17][CH2:16][CH:5]1[CH2:4][CH2:3][CH:2]=[CH:6]1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 72973-Chlorocyclopent-1-eneHCID 5462224MagnesiumHCID 13924075(3-Chloro-1-ethylpropoxy)(1,1-dimethylethyl)dimethylsilaneHCID 53804206(5-Chloro-3-pentyloxy)(2,2-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-1330f36ba32940c0b11208389e6b76ff
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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