Hydrogen Peroxide → 4,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1,1-dioxide

HRID 402812Notes

Reaction equation

HRID 402812 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[S:5](=[O:14])[CH2:4][CH2:3]1.C1C[O:19]CC1.OO>C(O)C.ClCCl.[NH4+].[Cl-].[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=2)[S:5](=[O:19])(=[O:14])[CH2:4][CH2:3]1

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 866852694,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1-oxide

Product 1

HCID 866852704,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1,1-dioxide

Reagents, catalysts & solvents 4

HCID 61578Diammonium molybdateCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 4,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde 1-oxide (148 mg, 0.67 mmol) in ethanol (5.94 mL): THF (2.40 mL) and hydrogen peroxide (2.33 mL, 26.6 mmol, 35 wt. % in water) was treated with ammonium molybdate (26.1 mg, 0.13 mmol) at room temperature. The mixture was stirred at room temperature for 80 minutes before being diluted with dichloromethane (30.0 mL) and saturated aqueous NH4Cl (5.00 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (2×, 30.0 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-5% MeOH/dichloromethane to give the desired product as a white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×, 30.0 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude mixture was purified by silica gel chromatography
  7. washeluting with 0-5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-14d15f788af9422782cb35ea4e21da9f
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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