Imidazole → HCID 69142436, compound

HRID 1766856Notes

Reaction equation

HRID 1766856 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].N1C=CN=[CH:10]1.[C:14]1(=[O:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][O:15]1.[OH2:24]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Si:5]([O:24][CH2:10][C:20]1[CH:21]=[C:22]2[C:17]([CH2:16][O:15][C:14]2=[O:23])=[CH:18][CH:19]=1)([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 6885PhthalideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 69142436HCID 69142436, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butylchlorodimethylsilane (647.3 mg, 4.30 mmol) and imidazole (292.3 mg, 4.30 mmol) were added to 6-(hydroxymethyl)-[(3H)-isobenzofuranone (587.5 mg, 3.58 mmol) obtained from Example 1-(4) or Example 1-(6) in N,N-dimethylformamide (10 ml). After the mixture was stirred at room temperature for 1 hour, water (20 ml) was added thereto, and then the product was extracted with a mixed solvent of ethyl acetate and hexane. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to afford an oily residue. The residue was subjected to chromatography on a silica gel (25 g) column (eluent; ethyl acetate:hexane=1:10˜1:1) to give the title compound (940.1 mg, 94% yield) as a colorless oil.

Workup

  1. extractionthe product was extracted with a mixed solvent of ethyl acetate and hexane
  2. washThe organic layer was washed with water
  3. distillationwith a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure
  4. customto afford an oily residue

Sources & evidence

ORD record
ord-3d9a9570a3674683b69386ff682d259b
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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