Phosphoric Acid → 2-(4-Methylsulfonylphenyl)-1-phenylazulene

HRID 1456822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1456822
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2C(OC)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].P(=O)(O)(O)O>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[C:13]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=[CH:14]3)[C:20]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Komponenten

3

Edukt 2

HCID 1004Phosphoric AcidHCID 22107203Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate

Produkt 1

HCID 221071632-(4-Methylsulfonylphenyl)-1-phenylazuleneAusbeute 89,4 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate(0.13 g) was treated with 100% phosphoric acid (5.0 ml). After stirring for 10 min at 120° C., the reaction mixture was poured into ice-water, followed by extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4 and concentrated. The crude product was purified by SiO2 column chromatography (benzenee/Et2O, 50: 1) to give the title compound (0.10 g) as violet crystals; mp 139°-140° C.

Aufarbeitung

  1. extractionby extracted with EtOAc
  2. washThe combined EtOAc extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by SiO2 column chromatography (benzenee/Et2O, 50: 1)

Quellen und Nachweise

ORD-Eintrag
ord-4450231d752345ca9a88b2df2f88f361
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843999

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