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

HRID 389447Notes

Reaction equation

HRID 389447 reaction equation
[CH:1]1([OH:7])[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O>CN(C=O)C>[Si:13]([O:6][CH:3]1[CH2:4][CH2:5][CH:1]([OH:7])[CH2:2]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 100165Cyclopentane-1,3-diol

Product 1

HCID 21938628Cyclopentanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-Yield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,3-cyclopentanediol (5 g, 49 mmol) and imidazole (5 g, 74 mmol) in DMF (20 mL) added tert-butyldimethylsilyl chloride (5.9 g, 39 mmol). The reaction stirred for 3 h at room temperature and was then poured into water and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (10% diethyl ether:hexanes) to afford 3.5 g (33%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 4.3-4.5 (m, 2H), 1.9-2.15 (m, 2H), 1.65-1.8 (m, 2H), 1.4-1.6 (m, 2H), 1.32-1.41 (m, 1H), 0.86 (s, 9H), 0.05 (s, 6H).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (10% diethyl ether:hexanes)

Sources & evidence

ORD record
ord-3542e0b6604f493794e3af55e5e006c2
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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