Water → Ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylsulfonyl)naphthalenyl)ethenyl]benzoate

HRID 1953868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953868
[CH3:1][C:2]1([CH3:32])[CH2:11][CH:10]=[C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]2[C:7](/[CH:19]=[CH:20]/[C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)=[CH:6][CH:5]=[CH:4][C:3]1=2.ClC1C=C(C=CC=1)C(OO)=[O:38].[OH2:44]>C(Cl)Cl>[CH3:32][C:2]1([CH3:1])[CH2:11][CH:10]=[C:9]([S:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:38])=[O:44])[C:8]2[C:7](/[CH:19]=[CH:20]/[C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=3)=[CH:6][CH:5]=[CH:4][C:3]1=2

Komponenten

5

Edukt 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 19695074Ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylthio)naphthalenyl)ethenyl]benzoate

Produkt 1

HCID 19695082Ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylsulfonyl)naphthalenyl)ethenyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 0.090 g (0.2 mmol) of ethyl (E)4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylthio)-naphthalenyl)ethenyl]benzoate (Compound A16) in 2.0 mL of methylene chloride was added dropwise a solution of 140 mg (0.45 mmol, 50-60 %) of m-chloroperoxybenzoic acid in 2.0 mL of methylene chloride and the reaction stirred at room temperature for 3.5 h. The mixture was diluted with water and extracted with methylene chloride (2x). The organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica, 30% ethyl acetate in hexanes) followed by recrystallization in EtOH to afford the title compound as a solid.

Aufarbeitung

  1. extractionextracted with methylene chloride (2x)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (silica, 30% ethyl acetate in hexanes)
  5. customfollowed by recrystallization in EtOH

Quellen und Nachweise

ORD-Eintrag
ord-2ffbb81e330145a1b8f9cd6e1ac418cb
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117987

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