1,6-Dibromohexane → {2-[(6-Bromohexyl)oxy]ethoxy}(tert-butyl)dimethylsilane

HRID 2116931Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

2-{[tert-Butyl(dimethyl)silyl]oxy}ethanol (1.82 g), 1,6-dibromohexane (7.56 g) and tetrabutylammonium bromide (0.067 g) were stirred under nitrogen and treated with 50% w/v sodium hydroxide (2 g in 4 ml). The mixture was stirred vigorously at 20° C. for 5 days. Water (100 ml) was added, and the product extracted with dichloromethane (3×50 ml). The combined organic layer was separated and dried over Na2SO4 before filtering. The solvent was evaporated in vacuo to give a residue which was purified by flash chromatography on silica. Elution with 5% ether/cyclohexane followed by solvent evaporation in vacuo gave the title compound (2.35 g). LCMS RT=4.32 min, ES+ve 339 (MH)+.

Workup

extractionthe product extracted with dichloromethane (3×50 ml)
customThe combined organic layer was separated
dry with materialdried over Na2SO4
filtrationbefore filtering
customThe solvent was evaporated in vacuo
customto give a residue which
customwas purified by flash chromatography on silica
washElution with 5% ether/cyclohexane
customfollowed by solvent evaporation in vacuo

Sources & evidence

ORD record: ord-1b8a472988ea485c95ef1f70821a9dfb
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439393B2

Reaction notes

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