Imidazole → HCID 77141853, compound

HRID 444805Notes

Reaction equation

HRID 444805 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH2:11][CH:12]([OH:15])[CH2:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]1[CH2:11][CH:12]([O:15][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27])[CH2:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 16079232HCID 16079232, compound

Product 1

HCID 77141853HCID 77141853, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 3-(benzyloxymethyl)cyclopent-3-enol (CAS 153186-83-5; Nucleosides, Nucleotides, and Nucleic Acids 26: 935-37, 2007) (5.75 g, 28.1 mmol) and imidazole (2.87 g, 42.2 mmol) in dry N,N-dimethylformamide (20 ml) at 0° C. was added tert-butyldimethylchlorosilane (5.09 g, 33.8 mmol). Stiffing was continued at 0° C. for 5 minutes, the cooling bath was removed and the mixture was stirred at 23° C. for 2 h. For the workup, the reaction mixture was poured into water, followed by extraction with TBME. The organic layer was washed with brine and dried over Na2SO4. Removal of the solvent at reduced pressure left a yellow oil, which was purified by flash chromatography (silica gel, 50 g, 0% to 15% EtOAc in heptane) to give the (3-(benzyloxymethyl)cyclopent-3-enyloxy)(tert-butyl)dimethylsilane (7.3 g, 81.4% yield) as a colorless liquid.

Workup

  1. customthe cooling bath was removed
  2. additionFor the workup, the reaction mixture was poured into water
  3. extractionfollowed by extraction with TBME
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent at reduced pressure
  7. waitleft a yellow oil, which
  8. customwas purified by flash chromatography (silica gel, 50 g, 0% to 15% EtOAc in heptane)

Sources & evidence

ORD record
ord-9add52c8659649b59892a559677cf615
Source dataset
uspto-grants-2013_07
Patent number
US08476264B2

Reaction notes

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