tert-Butyl hydroperoxide → HCID 67279428, compound

HRID 1694667Notes

Reaction equation

HRID 1694667 reaction equation
[C:1]([O:5][P:6]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][C:27]4[N:28]=[C:29]([C:32]5[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=5)[O:30][CH:31]=4)=[CH:20][CH:21]=3)[O:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([O:52]O)(C)(C)C.S(=O)(O)[O-].[Na+]>O1CCCC1.C(#N)C.CCCCCCCCCC>[P:6]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][C:27]4[N:28]=[C:29]([C:32]5[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([C:39]([F:42])([F:40])[F:41])[CH:33]=5)[O:30][CH:31]=4)=[CH:20][CH:21]=3)[O:16][CH:15]=2)=[CH:10][CH:9]=1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:52]

Participants

7

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 23665763Sodium BisulfiteHCID 67279775HCID 67279775, compound2×

Product 1

HCID 67279428HCID 67279428, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 15600DecaneSolvent

Procedure

To a solution of the product of step 1, 3-{4-[bis(tert-butoxy)phosphinooxy]phenyl}-7-({2-[5-fluoro-3-(trifluoromethyl)phenyl](1,3-oxazol-4-yl)}methoxy)chromen-4-one, in a mixture of tetrahydrofuran (20 mL) and acetonitrile (10 mL) was added 6 mL of tert-butyl hydroperoxide in decane (5M-6M). The reaction mixture was stirred at room temperature for 1 hour, chilled in an ice bath, and 50 mL of 5% sodium bisulfite was added. The resulting mixture was stirred for 15 minutes, after which the ice bath was removed. The mixture was extracted with methylene chloride, the organic extract dried over sodium sulfate, and solvent removed under reduced pressure. The residue was purified by biotage column chromatography, eluting with 1:1 ethyl Acetate/hexanes mixture, to afford ditert-butyl 4-[7-({2-[5-fluoro-3-(trifluoromethyl)phenyl](1,3-oxazol-4-yl)}methoxy)-4-oxochromen-3-yl]phenyl phosphate.

Workup

  1. temperaturechilled in an ice bath
  2. stirringThe resulting mixture was stirred for 15 minutes
  3. customafter which the ice bath was removed
  4. extractionThe mixture was extracted with methylene chloride
  5. extractionthe organic extract
  6. dry with materialdried over sodium sulfate, and solvent
  7. customremoved under reduced pressure
  8. customThe residue was purified by biotage column chromatography
  9. washeluting with 1:1 ethyl Acetate/hexanes mixture

Sources & evidence

ORD record
ord-b7b835d29f00461388a07bc284e9ad05
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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