Imidazole → 2-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 2371850Notes

Reaction equation

HRID 2371850 reaction equation
CN(C)[CH:3]=[O:4].N1[CH:10]=[CH:9]N=C1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C([O:21][CH2:22][CH3:23])C>>[Si:11]([O:21][CH:22]1[CH2:23][CH:3]([OH:4])[CH:10]=[CH:9]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 127633552-Cyclopenten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

Procedure

To 1.592 g (15.9 mmol) of the oil, prepared as described in the preceding paragraph, was added successively 20 mL dimethylformamide, 1.51 g (22.3 mmol) imidazole, and 2.39 g (15.9 mmol) t-butyldimethylsilyl chloride. The resulting solution was stirred for 12 hrs, diluted with 100 mL of diethyl ether, and extracted 6×(i.e., six times), each with 2 mL water. The organic phase was dried over MgSO4, filtered, and concentrated. Chromatography on a 2×18 cm column, packed with hexane and eluted with 100 mL each of 2%, 4%, 6%, 10%, 15%, and 20% ethyl acetate/hexane provided 683 mg clear colorless oil in 12 mL fractions 26-35.

Workup

  1. extractionextracted 6×(i.e., six times)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluted with 100 mL each of 2%, 4%, 6%, 10%, 15%, and 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8d61a12a3b4742a8ab2fcf30416819e5
Source dataset
uspto-grants-1992_03
Patent number
US05096838

Reaction notes

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