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

HRID 1160292노트

반응식

HRID 1160292 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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 sonicated 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).

후처리

  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

출처 및 근거

ORD 기록
ord-ced32dbf73924ae3bb78d09126a664ec
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816367B2

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