tert-Butyl hydroperoxide → HCID 17862558, compound

HRID 1766876Notes

Reaction equation

HRID 1766876 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:11].[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:3]1[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=1[C:6]([O:5][CH2:4][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 4686855Diallyl diisopropylphosphoramiditeHCID 126495194-fluoroisobenzofuran-1(3H)-oneHCID 178418441HCID 178418441, compound

Product 1

HCID 17862558HCID 17862558, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to a similar procedure to that described in Example 4-(5), 4-fluoro-1(3H)-isobenzofuranone (described in Tetrahedron, 54, 7485 (1998); 1.52 g, 10 mmol) was reacted with an aqueous solution of sodium hydroxide (1.008N; 10 ml, 10 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); 3.43 g, 14 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 residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate:hexane=2:3) to afford an oily mixture. The mixture was further subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=1:2) to afford the title compound (1.40 g, 31% yield) as a colorless oil.

Workup

  1. customto afford
  2. extractionafter extraction
  3. customto afford an oily mixture

Sources & evidence

ORD record
ord-de04568355dd441ab461298bb246b206
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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