Bis(trimethylsilylmethyl) sulfoxide → 5-(4'-Chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione

HRID 40473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40473
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:17])[CH:15]=[CH:14][C:13]3=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.C[Si]([CH2:27][S:28]([CH2:30][Si](C)(C)C)=O)(C)C>CN1CCCN(C)C1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:17])[CH:15]4[CH2:27][S:28][CH2:30][CH:14]4[C:13]3=[O:18])[CH:11]=2)=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 13694173Bis(trimethylsilylmethyl) sulfoxideHCID 497657352-(4'-Chloro-4-ethylbiphenyl-3-yl)cyclopent-4-ene-1,3-dione

Produkt 1

HCID 497657365-(4'-Chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 2-(4′-chloro-4-ethylbiphen-3-yl)cyclopent-4-ene-1,3-dione (0.200 g, 0.65 mmol) and crude bis(trimethylsilylmethyl)sulphoxide (0.406 g, 0.97 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (3 ml) is heated at 100° C. for 20 minutes under microwave irradiation. The reaction mixture is then partitioned between diethylether and distilled water, and the organic phase is washed with water (×2) then brine. After drying over magnesium sulfate the crude mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is purified by preparative reverse phase HPLC to afford 5-(4′-chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione.

Aufarbeitung

  1. customThe reaction mixture is then partitioned between diethylether
  2. distillationdistilled water
  3. washthe organic phase is washed with water (×2)
  4. dry with materialAfter drying over magnesium sulfate the crude mixture
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue is purified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f1dd7b843eee4992a79052391d8a5eed
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530388B2

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