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

HRID 402812ノート

反応式

HRID 402812 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 61578Diammonium molybdate触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-14d15f788af9422782cb35ea4e21da9f
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

反応ノート

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