Imidazole → (trans)-2-(t-Butyldimethysiloxy)-cyclopentanol

HRID 3142

Reaction equation

HRID 3142 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[C@@H:14]1([OH:20])[CH2:18][CH2:17][CH2:16][C@H:15]1[OH:19]>CN(C=O)C>[O:19]([C@@H:15]1[CH2:16][CH2:17][CH2:18][C@H:14]1[OH:20])[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 225711trans-1,2-Cyclopentanediol

Product 1

HCID 70100529(trans)-2-(t-Butyldimethysiloxy)-cyclopentanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To a mixture of t-butyldimethylsilyl chloride (5.08 g, 33.7 mmol) and imidazole (2.30 g, 33.7 mmol) in DMF (10 mL), a solution of trans-1,2-cyclopentanediol in DMF (4 mL) was added. The reaction mixture was stirred overnight at 25° C. The reaction mixture was diluted with ice water and extracted with ether. The ether extract was washed with water and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, 9:1 hexane:ethyl acetate) to the title compound as an oil (3.44 g, 49%).

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by flash chromatography (silica, 9:1 hexane:ethyl acetate) to the title compound as an oil (3.44 g, 49%)

Sources & evidence

ORD record
ord-b0f251ba8a8b43138ec22405d9b99942
Source dataset
uspto-grants-1998_03
Patent number
US05733882

Linked notes

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