Imidazole → (3-Benzyloxy-cyclobutylmethoxy)-tert-butyl-dimethylsilane

HRID 1907315Notes

Reaction equation

HRID 1907315 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C)C=O>[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([CH2:13][O:14][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 15221213(3-(Benzyloxy)cyclobutyl)methanol

Product 1

HCID 66780081(3-Benzyloxy-cyclobutylmethoxy)-tert-butyl-dimethylsilaneYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3-Benzyloxy-cyclobutyl)-methanol (1.46 g) in N,N-dimethylformamide was treated at 0° C. with imidazole (1.55 g) and tert-butyldimethylsilyl chloride (1.37 g) and allowed to warm to room temperature over 16 hours. The reaction mixture was extracted with ethyl acetate, the organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (0 to 1:9 by volume) to give the title compound (2.24 g).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate in cyclohexane (0 to 1:9 by volume)

Sources & evidence

ORD record
ord-86a24abc55c04ed29763a1262c536027
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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