p-Toluenesulfonic acid → 2,2-Dimethyl-5-[4-(2-methyl-benzylsulfanyl)-benzylidene]-[1,3]dioxane-4,6-dione

HRID 1993041Notes

Reaction equation

HRID 1993041 reaction equation
N1CCCC1.[CH3:6][C:7]1[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=1[CH2:9][S:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[CH3:23][C:24]1([CH3:32])[O:31][C:29](=[O:30])[CH2:28][C:26](=[O:27])[O:25]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[CH3:23][C:24]1([CH3:32])[O:31][C:29](=[O:30])[C:28](=[CH:15][C:14]2[CH:17]=[CH:18][C:11]([S:10][CH2:9][C:8]3[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=3[CH3:6])=[CH:12][CH:13]=2)[C:26](=[O:27])[O:25]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31268PyrrolidineHCID 591327064-(2-Methyl-benzylsulfanyl)-benzaldehyde

Product 1

HCID 591326082,2-Dimethyl-5-[4-(2-methyl-benzylsulfanyl)-benzylidene]-[1,3]dioxane-4,6-dioneYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Pyrrolidine (0.45 mL, 5.27 mmol) was added to a solution of aldehyde 28.1 in diethyl ether (20 mL) and the mixture was sonicated for 5 minutes. The mixture was then added to a solution of Meldrum's acid (0.73 g, 5.08 mmol) in diethyl ether (20 mL) and the resultant mixture was sonciated for 5 minutes, forming a solid. The solid was filtered, rinsed with diethyl ether, and then suspended in DCM (10 mL). p-Toluenesulfonic acid (0.97 g, 5.10 mmol) was then added to the suspension and the suspension was sonicated until clear. The solvent was removed under reduced pressure, and the resulting residue was taken up in diethyl ether and partitioned between water and ethyl acetate. The aqueous layer was extracted 2 additional times with ethyl acetate. The combined organic layers were washed with water, dried (Na2SO4), and concentrated in vacuo to yield 1.05 g (54%) of 2,2-Dimethyl-5-[4-(2-methyl-benzylsulfanyl)-benzylidene]-[1,3]dioxane-4,6-dione (28.2) as a yellow oil The resulting yellow oil was used without further purification. LC/MSD m/e: 391.1 (M+Na).

Workup

  1. customthe mixture was sonicated for 5 minutes
  2. customforming a solid
  3. filtrationThe solid was filtered
  4. washrinsed with diethyl ether
  5. customthe suspension was sonicated until clear
  6. customThe solvent was removed under reduced pressure
  7. custompartitioned between water and ethyl acetate
  8. extractionThe aqueous layer was extracted 2 additional times with ethyl acetate
  9. washThe combined organic layers were washed with water
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-889d8d81f7ff4a5fae911fa56792d327
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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