m-Chloroperbenzoic acid → 4,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1-oxide

HRID 402811Notes

Reaction equation

HRID 402811 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[S:5][CH2:4][CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>ClCCl>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[S:5](=[O:23])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 152843084,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde

Product 1

HCID 866852694,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4,4-Dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde (449 mg, 2.18 mmol, Example 5-28, Step 2) was dissolved in dichloromethane (22.0 mL) and mCPBA (751 mg, 4.35 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 30 minutes. The mixture was then diluted with dichloromethane, washed with saturated aqueous NaHCO3, saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-5% MeOH/dichloromethane to afford the desired product as a colorless oil.

Workup

  1. washwashed with saturated aqueous NaHCO3, saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude mixture was purified by silica gel chromatography
  6. washeluting with 0-5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-197c1b7920374bb1a1e4e23e2dcca3ce
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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