Imidazole → 4-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutan-1-ol

HRID 1968913Notes

Reaction equation

HRID 1968913 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1COCC1>[Si:14]([O:7][CH2:6][CH2:5][C:2]([CH3:8])([CH3:1])[CH2:3][OH:4])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 108878792,2-Dimethylbutane-1,4-diol

Product 1

HCID 197346474-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutan-1-olYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 9A (0.80 g, 6.8 mmol) and imidazole (0.462 g) in THF (8.0 mL) at room temperature was added tert-butyldimethylsilyl chloride (1.02 g), and the solution was stirred for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with a gradient starting with 33% hexanes in chloroform and ending with 25% ethyl acetate in chloroform, to give the title compound (1.153 g, 73%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with a gradient

Sources & evidence

ORD record
ord-3b84396153d94f2faa1e0b32ec4fb27d
Source dataset
uspto-grants-2013_04
Patent number
US08426388B2

Reaction notes

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