m-Chloroperbenzoic acid → HCID 72410012, compound

HRID 2261039Notes

Reaction equation

HRID 2261039 reaction equation
[Si]([O:8][CH:9]1[CH2:14][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH:11]=[CH:10]1)(C(C)(C)C)(C)C.C1C=C(Cl)C=C(C(OO)=[O:28])C=1>C(Cl)Cl>[OH:28][CH:11]1[CH:10]2[CH:9]([O:8]2)[CH2:14][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 72410009HCID 72410009, compound

Product 1

HCID 72410012HCID 72410012, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 239D (25.2 g, 88.3 mmol) in 250 mL of CH2Cl2 at 0° C. was added solid m-CPBA (39.6 g, 176.6 mmol, 77% max) in small portions while the internal temperature was kept below 0° C. during the addition. The mixture was stirred at 0° C. for 30 min and then room temperature for 4.0 hrs. More solid m-CPBA (39.6 g, 176.6 mmol, 77% max) was added in small portions and the mixture was stirred at room temperature for three days. The precipitate was removed by filtration and the filtrate was washed with 20% Na2S2O3 (500 mL×3), sat'd NaHCO3 (500 mL×3) and brine (250 mL), dried over anhydrous Na2SO4. Purification by flash chromatography (hexane-EtOAc: 9.5:0.5 to 9:1) on silica gel afforded 4.33 g of 239E (lower Rf) as an oil.

Workup

  1. additionwas kept below 0° C. during the addition
  2. waitroom temperature for 4.0 hrs
  3. stirringthe mixture was stirred at room temperature for three days
  4. customThe precipitate was removed by filtration
  5. washthe filtrate was washed with 20% Na2S2O3 (500 mL×3), sat'd NaHCO3 (500 mL×3) and brine (250 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customPurification by flash chromatography (hexane-EtOAc: 9.5:0.5 to 9:1) on silica gel

Sources & evidence

ORD record
ord-ae8f717c154c485cb7825bac7d3d6c03
Source dataset
uspto-grants-2010_12
Patent number
US07846931B2

Reaction notes

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