Imidazole → tert-Butyl[(furan-2-yl)methoxy]dimethylsilane

HRID 402218Notes

Reaction equation

HRID 402218 reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].N1C=CN=C1>CN(C)C=O>[Si:8]([O:7][CH2:1][C:2]1[O:6][CH:5]=[CH:4][CH:3]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 7361Furfuryl AlcoholHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10976930tert-Butyl[(furan-2-yl)methoxy]dimethylsilaneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 1 liter flask containing dimethyl formamide (150 mL) was added furfuryl alcohol (17.7 mL, 0.20 mol), t-butyldimethylsilyl chloride (33.7 g, 0.22 mole), and imidazole (15.3 g, 0.22 mol). After 22 hours stirring at RT, the reaction was filtered and the volatiles removed in vacuo. The resulting material was partitioned between diethyl ether (500 mL) and a saturated aqueous solution of citric acid (100 mL). Additionally, the ether layer was washed 2×100 mL sat. citric acid. The combined aqueous layers were back extracted 1×50 mL ether. The combined organic layers were washed 1×100 mL water followed by 1×100 mL brine. The ether layer was dried over anhydrous sodium sulfate, filtered, and evaporated to yield 28.1 g (65% yield). 1H NMR: (DMSO-d6) δ 0.01 (s, 6H), 0.82 (s, 9H), 4.55 (s, 2H), 6.29 (d, 1H), 6.36 (dd, 1H), 7.58 (d, 1H)

Workup

  1. filtrationthe reaction was filtered
  2. customthe volatiles removed in vacuo
  3. customThe resulting material was partitioned between diethyl ether (500 mL)
  4. washAdditionally, the ether layer was washed 2×100 mL sat. citric acid
  5. extractionThe combined aqueous layers were back extracted 1×50 mL ether
  6. washThe combined organic layers were washed 1×100 mL water
  7. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto yield 28.1 g (65% yield)

Sources & evidence

ORD record
ord-07fce048ace04f058407913a92a82004
Source dataset
uspto-grants-2014_06
Patent number
US08742086B2

Reaction notes

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