tert-Butyl hydroperoxide → HCID 17862533, compound

HRID 1766874Notes

Reaction equation

HRID 1766874 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[CH2:4][O:3]1.[OH-:13].[Na+].C[O:16][C:17]1C=CC(CCl)=CC=1.N1C=NN=N1.[CH2:30]([O:33][P:34]([O:42][CH2:43][CH:44]=[CH2:45])N(C(C)C)C(C)C)[CH:31]=[CH2:32].[C:46]([O:50]O)(C)(C)C.[CH3:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]>C(OCC)(=O)C>[CH2:43]([O:42][P:34]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[CH:9][C:10]=1[C:2]([O:50][CH2:46][C:54]1[CH:53]=[CH:52][C:57]([O:16][CH3:17])=[CH:56][CH:55]=1)=[O:1])([O:33][CH2:30][CH:31]=[CH2:32])=[O:13])[CH:44]=[CH2:45]

Participants

9

Reactant 7

HCID 6410tert-Butyl hydroperoxideHCID 8058Hexane2×HCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 4686855Diallyl diisopropylphosphoramiditeHCID 132895623-Oxo-1,3-dihydro-2-benzofuran-5-carbonitrileHCID 178418441HCID 178418441, compound

Product 1

HCID 17862533HCID 17862533, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

According to a similar procedure to that described in Example 4-(5), 1-oxo-1,3-dihydroisobenzofuran-6-carbonitrile (1.66 g, 10.5 mmol) obtained from Example 5-(2) was reacted with an aqueous solution of sodium hydroxide (1.008N; 10.38 ml, 10.46 mmol), 4-methoxybenzyl chloride (1.64 g, 10.5 mmol), tetrazole (1.47 g, 20.9 mmol), bis(allyloxy)(diisopropylamino)phosphine (Tetrahedron Lett., 30, 4219 (1989); 3.68 g, 15 mmol), and tert-butyl hydroperoxide (80% di-tert-butyl peroxide solution; Merck; 2.7 g, 24 mmol), and the reaction mixture was worked up to afford, after extraction, a residue as a mixture of a solid (starting material) and an oil. The residue was washed with a mixed solvent of ethyl acetate-hexane, and the washings were concentrated to give a residue. The residue was subjected to chromatography on a silica gel (40 g) column (eluent; ethyl acetate:hexane=1:1˜3:2) to afford a mixture of a solid and an oily material. The mixture was washed further with a mixed solvent of ethyl acetate-hexane, and the washings were concentrated to give a residue. The residue was subjected to chromatography on a silica gel (40 g) column (eluent; ethyl acetate:hexane=2:3) to afford the title compound (737.9 mg, 15% yield) as a colorless oil.

Workup

  1. customto afford
  2. extractionafter extraction
  3. additiona residue as a mixture of a solid (starting material)
  4. washThe residue was washed with a mixed solvent of ethyl acetate-hexane
  5. concentrationthe washings were concentrated
  6. customto give a residue
  7. customto afford
  8. additiona mixture of a solid
  9. washThe mixture was washed further with a mixed solvent of ethyl acetate-hexane
  10. concentrationthe washings were concentrated
  11. customto give a residue

Sources & evidence

ORD record
ord-2d6fc06e46324de183569e5e2d2ddd4c
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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