Potassium Iodide → HCID 22858127, compound

HRID 2260837Notes

Reaction equation

HRID 2260837 reaction equation
C1(S[CH2:8][C@H:9]([C:11]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH3:10])C=CC=CC=1.Cl[C:18]1[CH:23]=[CH:22][CH:21]=[C:20](C(OO)=O)[CH:19]=1.[S:28]([O-:32])([O-])(=[O:30])=S.[Na+].[Na+].[I-].[K+]>ClCCl.C(=O)(O)[O-].[Na+]>[C:18]1([S:28]([CH2:8][C@H:9]([C:11]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH3:10])(=[O:32])=[O:30])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 22858126HCID 22858126, compound

Product 1

HCID 22858127HCID 22858127, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred and ice-cooled mixture of 5a (2.06 g, 8.71 mmol) in dichloromethane (19 mL) and saturated sodium bicarbonate solution (28 mL) was added m-chloroperbenzoic acid (85%, 4.24 g, 20.9 mmol) portionwise. The mixture was stirred in an ice bath for 50 min. An excess amount of peracid was decomposed with sodium thiosulfate solution in the presence of a small amount of potassium iodide. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with sodium bicarbonate solution and brine, and dried over sodium sulfate. Filtration and concentration gave 3.16 g of an oily material, which was purified by column chromatography (silica gel 32 g, ethyl acetate in n-hexane, 20-33%) to give 2.43 g (quantitative) of 6a, as a colorless oil.

Workup

  1. temperatureice-cooled
  2. stirringThe mixture was stirred in an ice bath for 50 min
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-464f23098c23444f853bf14033b29cb7
Source dataset
uspto-grants-1995_12
Patent number
US05478955

Reaction notes

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