Imidazole → Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, trans-

HRID 1993868Notes

Reaction equation

HRID 1993868 reaction equation
[CH:1]1([OH:5])[CH:3]([OH:4])[CH2:2]1.N1[CH:10]=[CH:9]N=C1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>CN(C=O)C.[Cl-].[Na+].O>[C:14]([Si:11]([CH3:13])([CH3:12])[O:5][C@H:1]1[CH2:10][CH2:9][C@H:3]([OH:4])[CH2:2]1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 186993271,3-Cyclopropanediol

Product 1

HCID 58715064Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, trans-Yield 54.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 1,3-cyclopropanediol (5 g, 49 mmol) and imidazole (5 g, 73.4 mmol) in DMF (20 mL) was added t-butyldimethylsilyl chloride (5.2 g, 34.5 mmol) and the mixture was stirred for 90 minutes at room temperature. The mixture was diluted with brine (200 mL) and extracted with ether three times (1×100 mL and 2×50 mL). Each extract was washed with a portion of brine. The organic phases were combined, dried over sodium sulfate and evaporated to dryness. The mixture of cis/trans isomers was purified by column chromatography using ether and hexanes to give the predominant trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol as a colorless liquid (4.1 g).

Workup

  1. extractionextracted with ether three times (1×100 mL and 2×50 mL)
  2. washEach extract was washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. additionThe mixture of cis/trans isomers
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-235cd75dbb4947a59f15230ae65ab638
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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