m-Chloroperbenzoic acid → HCID 71038080, compound

HRID 2361715Notes

Reaction equation

HRID 2361715 reaction equation
[C:1]([O-:4])([OH:3])=O.[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1.O=[C:18]1[CH:25]2[CH2:26][C:21]3([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]3)C2.S(=O)(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:3]=[C:1]1[CH:25]2[CH2:26][C:21]3([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:20][CH:19]([CH2:27][CH:23]([CH2:22]3)[O:4]1)[CH2:18]2

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 58192767HCID 58192767, compound

Product 1

HCID 71038080HCID 71038080, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid NaHCO3 (0.3 mol) and mCPBA (0.3 mmol, 77% purity) were added to a solution of ketone 1C (0.19 mmol) in DCM (5 mL) t 0° C. The reaction mixture was allowed to warm to rt and was maintained for 1 h. The reaction mixture was diluted with a saturated, aqueous solution of sodium bisulfate (10 mL) and was extracted with DCM (3×5 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (10/90 to 30/70 EtOAC/hexane) to provide lactone 13A in 85% yield. Data: LC/MS (ESR) m/z 282 [M+1]+.

Workup

  1. temperaturewas maintained for 1 h
  2. extractionwas extracted with DCM (3×5 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (10/90 to 30/70 EtOAC/hexane)

Sources & evidence

ORD record
ord-fa85f3da1fe04f06a52fc61ff133b86e
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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