Imidazole → 3-((Tert-butyldimethylsilyl)oxy)-6-fluoro-1-indanone

HRID 362865Notes

Reaction equation

HRID 362865 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[C:4](=[O:12])[CH2:3]1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C)C=O>[Si:13]([O:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[C:4](=[O:12])[CH2:3]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 23293595HCID 23293595, compound

Product 1

HCID 232936503-((Tert-butyldimethylsilyl)oxy)-6-fluoro-1-indanoneYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-hydroxy-6-fluoro-1-indanone (4.09 g, 24.6 mmoles) in dimethylformamide (10 mL) was added to a solution of tert-butyldimethylsilyl chloride (4.60 g, 30.5 mmoles, Aldrich) and imidazole (4.22 g, 62.0 mmoles, Aldrich) in dimethylformamide (20 mL). The solution was stirred at ambient temperature for 18 hours and evaporated in vacuo. The residue was dissolved in dichloromethane (200 mL) and washed with water (6×75 mL) and brine (100 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane: ethyl acetate (95:5). The fractions containing the major spot were combined and evaporated in vacuo, and the residue was dried in a vacuum at ambient temperature for 18 hours to give 4.14 g (60%) of 3-((tert-butyldimethylsilyl)oxy)-6-fluoro-1-indanone as a white solid, mp 56°-58° C.;

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (200 mL)
  3. washwashed with water (6×75 mL) and brine (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with hexane: ethyl acetate (95:5)
  8. additionThe fractions containing the major spot
  9. customevaporated in vacuo
  10. customthe residue was dried in a vacuum at ambient temperature for 18 hours

Sources & evidence

ORD record
ord-bfa0b95239e54fc3a05e71f4c801dd00
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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