Sodium Iodide → Tert-butyl[2-chloro-1-(iodomethyl)ethoxy]dimethylsilane

HRID 1398133Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:14][Cl:15])(=O)=O)=CC=1.[I-:24].[Na+]>CC(C)=O>[C:20]([Si:17]([O:16][CH:13]([CH2:12][I:24])[CH2:14][Cl:15])([CH3:19])[CH3:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-{[tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate (20.3 g) in acetone (200 mL) was added sodium iodide (19.7 g), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with hexane. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (13.4 g).

Workup

concentrationThe reaction mixture was concentrated
additionwater was added to the residue
extractionthe mixture was extracted with hexane
dry with materialThe extract was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-139e8e51496a4863ac683f140d3771c7
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901309B2

Reaction notes

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