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

HRID 402812노트

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HRID 402812 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 61578Diammonium molybdate촉매HCID 702Ethanol용매HCID 6344Dichloromethane용매HCID 25517Ammonium Chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-14d15f788af9422782cb35ea4e21da9f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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