tert-Butyl hydroperoxide → HCID 17862496, compound

HRID 1766882Notes

Reaction equation

HRID 1766882 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[O:8][CH2:7]2.[OH-:12].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19](CCl)=[CH:18][CH:17]=1.N1C=NN=N1.[CH2:29]([O:32][P:33]([O:41][CH2:42][CH:43]=[CH2:44])N(C(C)C)C(C)C)[CH:30]=[CH2:31].[C:45]([O:49]O)(C)(C)C>CCCCCC.C(OCC)(=O)C>[CH2:42]([O:41][P:33]([O:49][CH2:45][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:10]=1[C:9]([O:8][CH2:7][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:23][CH:22]=1)=[O:11])([O:32][CH2:29][CH:30]=[CH2:31])=[O:12])[CH:43]=[CH2:44]

Participants

9

Reactant 6

HCID 6410tert-Butyl hydroperoxideHCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 34023357-Fluoro-1(3H)-isobenzofuranoneHCID 4686855Diallyl diisopropylphosphoramiditeHCID 178418441HCID 178418441, compound

Product 1

HCID 17862496HCID 17862496, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to a similar procedure to that described in Example 4-(5), 7-fluoro-1(3H)-isobenzofuranone (described in Tetrahedron, 54, 7485 (1998); 1.67 g, 11 mmol) was reacted with an aqueous solution of sodium hydroxide (1.008N; 10.9 ml, 11 mmol), 4-methoxybenzyl chloride (1.57 g, 10 mmol), tetrazole (1.40 g, 20 mmol), bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219 (1989); 3.1 g, 12.6 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, an oily residue. The oily residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate:hexane=2:3) to afford a mixture of a solid and an oily material. The mixture was washed with a mixed solvent of ethyl acetate and hexane, the washings were concentrated under reduced pressure to give a residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=1:4˜1:2) to afford the title compound (1.08 g, 24% yield) as a colorless oil.

Workup

  1. customto afford
  2. extractionafter extraction
  3. customto afford
  4. additiona mixture of a solid
  5. washThe mixture was washed with a mixed solvent of ethyl acetate and hexane
  6. concentrationthe washings were concentrated under reduced pressure
  7. customto give a residue

Sources & evidence

ORD record
ord-1ffd0dfcb11b48839c02c96799310d58
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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