tert-Butyl hydroperoxide → HCID 68871675, compound

HRID 494646Notes

Reaction equation

HRID 494646 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:24].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OO)(C)(C)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])([C:13]([N:15]([CH3:16])[CH3:17])=[O:14])[C:5]2[C:10]([C:11](=[O:24])[CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 2724130Cornforth reagentHCID 68874819HCID 68874819, compound

Product 1

HCID 68871675HCID 68871675, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the product of Example 169B (190 mg, 0.63 mmol) in benzene (4 mL) at room temperature under a N2 atmosphere was added 200 mg Celite® and pyridinium dichromate (474 mg, 1.26 mmol) followed by 70% tert-butyl hydroperoxide (175 μL, 1.26 mmol). The mixture was allowed to stir at room temperature for 1 hour, filtered through a pad of Celite® and the filtrate added to ethyl acetate (10 mL). The organic solution was washed with 5% Na2S2O5 (3× 10 mL) and with saturated NaCl (1× 10 mL) and dried over Na2SO4. The crude product was purified by column chromatography using 50% ethyl acetate in hexane. The title compound was obtained as a colorless oil (59 mg, 30%). 1H NMR (300 MHz, CDCl3): δ 8.18 (d, 1H), 7.56 (t, 1H), 7.44 (t, 1H), 7.26 (d, 1H), 5.98 (s, 1H), 3.85 (s, 3H), 2.95, 2.39 (dm, 3H), 2.42, 2.21 (dm, 2H), 1.56 (s, 3H), 1.32 (m, 1H), 0.73 (d, 3H), 0.65 (d, 3H), 0.28 (m, 2H). MS (ESI) m/z=316 [M+H].

Workup

  1. filtrationfiltered through a pad of Celite®
  2. additionthe filtrate added to ethyl acetate (10 mL)
  3. washThe organic solution was washed with 5% Na2S2O5 (3× 10 mL) and with saturated NaCl (1× 10 mL)
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e19635066019424b8e5da1f5608337e6
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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