Imidazole → 2-{[Tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate

HRID 71102Notes

Reaction equation

HRID 71102 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:16])[CH2:14][Cl:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CN=C1.[C:22]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([O:16][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27])[CH2:14][Cl:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 124610873-Chloro-2-hydroxypropyl 4-methylbenzenesulfonate

Product 1

HCID 866629712-{[Tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonateYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate (17.4 g) and imidazole (13.4 g) in DMF (130 mL) was added tert-butyl(chloro)dimethylsilane (14.9 g), and the mixture was stirred for 64 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, 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 (20.3 g).

Workup

  1. extractionthe mixture was extracted with hexane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c1b00079bedf4880986324ae8d87e8d5
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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