Imidazole → 3-Methyl-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazole

HRID 1011489Notes

Reaction equation

HRID 1011489 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][N:3]=1.CN(C=O)C.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1>CCOC(C)=O.C1(C)C=CC=CC=1.O>[Si:17]([O:11][C:9]1[CH:8]=[CH:7][C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH:10]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 1354978903-Methyl-1,2-benzisoxazol-6-ol

Product 1

HCID 231171073-Methyl-6-[(tert-butyl(dimethyl)silyl)oxy]-1,2-benzisoxazoleYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

3-methyl-1,2-benzisoxazol-6-ol (10 g, 67 mmoles) (prepared following M. A. Elkasaby, Indian J. Chem., 1987, 26, 620) and DMF (50 ml) were added to a mixture of tert-butyldimethylsilyl chloride (1.05 eq, 10.6 g), imidazole (2.5 eq, 11.4 g) and DMF (100 ml) under N2. The mixture was then stirred at room temperature for 1 h, poured into water and extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum to give a crude product. Flash chromatography (AcOEt/Toluene 18/85 with 0.1% TEA) gave 6-[(tert-butyl(dimethyl)silyl) oxy]-3-methyl-1,2-benzisoxazole (17.1 g, 97%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a crude product

Sources & evidence

ORD record
ord-c225e8c0a17e4e079400990675ed94f0
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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