Imidazole → 4-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-one

HRID 2363102Notes

Reaction equation

HRID 2363102 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(Cl)Cl.CCOC(C)=O>[C:20]([Si:17]([CH3:19])([CH3:18])[O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 158291994-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-oneYield 114.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-indan-1-one (1.0 g, 6.75 mmol) in CH2Cl2 (20 mL) was added imidazole (690 mg, 10.12 mmol). The mixture was stirred for 5 minutes, to which was added portionwise tert-butyldimethylsilyl chloride (1.05 g, 5.31 mmol). The mixture was stirred for 3 hours at room temperature and was diluted with EtOAc. The organic layer was washed with 1N HCl, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to give 4-(tert-butyl-dimethyl-silanyloxy)-indan-1-one (1600 mg, 90%).

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. washThe organic layer was washed with 1N HCl, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-28290f292fa84c1382bfe340ae71aec1
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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